Changes in the Binding of Hydrogen Ions in Enzyme-Catalyzed Reactions

Robert A. Alberty
Department of Chemistry 6-215
Massachusetts Institute of Technology
Cambridge, MA, USA
alberty@mit.edu

Abstract

Most enzyme-catalyzed reactions produce or consume hydrogen ions, and this is expressed by the change in the binding of hydrogen ions (Subscript[Δ, r]) (Subscript[N, H]) in the reaction, as written in terms of reactants (sums of species).  This property of a biochemical reaction is important because it determines the change in the apparent equilibrium constant K' with pH.  There are two rather diffferent ways to calculate (Subscript[Δ, r]) (Subscript[N, H]) for an enzyme-catalyzed reaction.  The first, which has been used for a long time, involves calculating the partial derivative of the standard transformed Gibbs energy of reaction with respect to pH. The second, which is described and used in this package, involves calculating the average number of hydrogen atoms in each reactant and adding and subtracting these average numbers to obtain (Subscript[Δ, r]) (Subscript[N, H]).  This package presents calculations of average numbers of hydrogen atoms in 199 biochemical reactants and uses them to calculate (Subscript[Δ, r]) (Subscript[N, H]) for 229 enzyme-catalyzed reactions at 298.15 K and 0.25 M ionic strength.  This database can be extended to include more reactants for which pKs are known or can be estimated.

1. Introduction

Most enzyme-catalyzed reactions produce or consume hydrogen ions, and this is expressed by the change in the binding of hydrogen ions (Subscript[Δ, r]) (Subscript[N, H]) in the reaction, as written in terms of reactants (sums of species).  This thermodynamic property of an enzyme-catalyzed reaction is important because it determines how the apparent equilibrium constant K' depends on pH.  If hydrogen ions are produced ((Subscript[Δ, r]) (Subscript[N, H]) < 0), raising the pH causes K' to increase, and if hydrogen ions are consumed ((Subscript[Δ, r]) (Subscript[N, H]) > 0), raising the pH causes K' to decrease.  This is an example of Le Chatelier's principle that if the conditions are changed on a system at equilibrium it will shift in the direction to oppose the change.  In Biochemical Thermodynamics: Applications of Mathematica (1) (Subscript[Δ, r]) (Subscript[N, H]) is calculated at 298.15 K and 0.25 M ionic strength for 229 enzyme-catalyzed reactions by using

(Subscript[Δ, r]) (Subscript[N, H]) = (1/RTln(10))((∂(Subscript[Δ, r])  G' °)/∂)pH												(1)

where (Subscript[Δ, r]) G' ° is the standard transformed Gibbs energy of reaction (see BasicBiochemData3.nb (2)), which is given by

(Subscript[Δ, r]) G' ° = -RTlnK'													(2)

This means that 

(Subscript[Δ, r]) (Subscript[N, H]) = - \(∂logK'\/∂pH\)													(3)

Thus when (Subscript[Δ, r]) (Subscript[N, H]) = -1 at a certain pH, the slope of the plot of logK' versus pH at that pH increases by a factor of 10 per pH unit.  In measuring thermodynamic properties of enzyme-catalyzed reactions it is assumed that the pH is held constant.  Therefore, biochemical reactions do not balance hydrogen atoms or electric charge.  

	However, there is a simpler way to obtain (Subscript[Δ, r]) (Subscript[N, H]) that does not depend on knowing the standard Gibbs energies of formation of all the species in a reaction.  This calculation is a two-step process.  First, the average number of hydrogen ions \(N\&_\_H\) in various reactants are calculated.  Second, these average values are added and subtracted to obtain (Subscript[Δ, r]) (Subscript[N, H]) for various biochemical reactions.
	The following symbols are used:
	
(Subscript[Δ, r]) G' ° 	Standard transformed Gibbs energy of reaction
(Subscript[N, H])(j)	Number of hydrogen atoms in species j
\(N\&_\_H\) (i)	Average number of hydrogen atoms in reactant i
(Subscript[Δ, r]) (Subscript[N, H])	Change in binding of hydrogen ions in an enzyme-catalyzed reaction
(Subscript[ν, i])' 	Stoichiometric coefficient of reactant i in an enzyme-catalyzed reaction
p	Binding polynomial
(Subscript[r, j]) 	Equilibrium mole fraction of species j 

The prime on (Subscript[ν, i])' indicates that the stoichiometric numbers are for biochemical reactions and not the underlying chemical reactions.  (Subscript[Δ, r]) G' °  is generally given in kJ (mol^(-1)), but the other properties are dimensionless.

2. Calculation of the average binding of hydrogen ions by a biochemical reactant

The calculation of the average binding of hydrogen ions by ATP as a function of pH and ionic strength is discussed on p. 29-32 in Biochemical Thermodynamics: Applications of Mathematica (1)  Since ATP is made up of three species in the range pH 5 to 9, its concentration is given by

[ATP] = [(ATP^(4-))] + [(HATP^(3-))] + [(Subscript[H, 2]) (ATP^(2-))]										(4)

When the acid dissociations are at equilibrium, substituting the expressions for the two acid dissociation constants yields

[ATP] = [(ATP^(4-))](1 + (10^(pK1ATP - pH)) + (10^(pK1ATP + pK2ATP - 2  pH)))								(5)

where (Subscript[pK, 1  ATP]) = - (Subscript[logK, 1  ATP]) is the highest pK that has to be considered in the range pH 5 to 9.  The factor multiplying [(ATP^(4-))] is referred to as a binding polynomial and is represented here by p.  Equation 5 shows that the equilibrium mole fraction (Subscript[r, 1]) for [(ATP^(4-))] is given by 

(Subscript[r, 1]) = 1/p														(6)

The other two equilibrium mole fractions are given by

(Subscript[r, 2]) = (10^(pK1ATP - pH))/p													(7)

(Subscript[r, 3]) = (10^(pK1ATP + pK2ATP - 2  pH))/p												(8)

The pKs are at the desired temperature and ionic strength.  The following calculations of the equilibrium concentrations of the species of ATP are for 298.15 K and 0.25 M ionic strength.

Off[General::"spell"];
Off[General::"spell1"];

patp = 
        1 + 10^(pK1ATP - pH) + 
          10^(pK1ATP + pK2ATP - 2*pH);

pK1ATP = 6.47;

pK2ATP = 3.83;

The equilibrium mole fractions of the three species of ATP are calculated using equations 6 to 8:

r1 = 1/patp;

r2 = 10^(pK1ATP - pH)/patp;

r3 = 10^(pK1ATP + pK2ATP - 2*pH)/patp;

Plot[{r1, r2, r3}, {pH, 3, 9}, 
        AxesLabel -> {"pH", "r"}];

Figure 1  Equilibrium mole fractions of the three species of ATP as functions of pH at 298.15 K and ionic strength 0.25 M

The (Subscript[r, 1]) curve for (ATP^(4-)), which has 12 hydrogen atoms, is on the right.  The (Subscript[r, 2]) curve in the middle is for (HATP^(3-)), which has 13 hydrogen atoms.  The (Subscript[r, 3]) curve on the left is for (Subscript[H, 2])(ATP^(2-)), which has 14 hydrogen atoms.  The average number of hydrogen atoms in a biochemical reactant is given by

\(N\&_\_H\) (i) = ∑(Subscript[r, j])(Subscript[N, H])(j)													(9)

The average number of hydrogen atoms in ATP is given by

nHATP = 12*r1 + 13*r2 + 14*r3;

In Mathematica * is the multiply sign.

\(\(Plot[{nHATP}, {pH, 3, 9}, 
        AxesLabel -> {"pH", \*""\!\(N\&_\_H\) ""}];\)\)

Figure 2  Titration curve for ATP at 298.15 K and ionic strength 0.25 M.

In contrast with the way titration curves are usually plotted, this plot gives the total number of hydrogen atoms.  
	The following program is used to derive the function of pH and ionic strength that will yield the average number of hydrogen atoms in a reactant with two dissociable hydrogen atoms.

\(\(calcavnoH[pK1_, pK2_, nHbasicform_] := 
        Module[{p, r1, r2, 
            r3},  (*This\ program\ derives\ the\ function\ of\ pH\ that\ gives\ the\ average\ number\ of\ hydrogen\ atoms\ in\ a\ reactant\ \ with\ three\ species . \ \ The\ pKs\ are\ for\ the\ desired\ temperature\ and\ ionic\ strength . \ \ nHbasicform\ is\ the\ number\ of\ hydrogen\ atoms\ in\ the\ species\ that\ dominates\ at\ the\ highest\ pH . \ \ If\ there\ is\ a\ single\ pK, \ 
            pK2\ can\ be\ set\ equal\ to\ zero . \ \ When\ there\ is\ a\ single\ species\ in\ the\ range\ pH\ 5\ to\ 9, \ 
            both\ pK1\ and\ pK2\ are\ set\ equal\ to\ \(\(zero\)\(.\)\)*) \ 
p = 
            1 + 10^\((pK1 - pH)\) + 
              10^\((pK1 + pK2 - 2*pH)\); 
r1 = 1/p; 

          r2 = 10^\((pK1 - pH)\)/p; 

          r3 = 10^\((pK1 + pK2 - 2*pH)\)/p; 
nHbasicform*
              r1 + \((nHbasicform + 1)\)*r2 + \((nHbasicform + 2)\)*
              r3];\)\)

The function of pH that yields \(N\&_\_H\)(ATP) is obtained as follows:

atpnhfun = calcavnoH[6.47, 3.83, 12]

Note that the function for ATP is named atpnhfun because the name atpNH is already used in BasicBiochemData3.nb (2) for the average number of hydrogen atoms in ATP calculated from its standard transformed Gibbs energy of formation.

\(\(Plot[{atpnhfun}, {pH, 3, 9}, 
        AxesLabel -> {"pH", \*""\!\(N\&_\_H\) ""}];\)\)

Figure 3 This is the same plot as in Figure 2 that was obtained without using the program calcavnoH.

The function of pH that yields \(N\&_\_H\)(ADP) is obtained as follows:

adpnhfun = calcavnoH[6.33, 3.79, 12];

The function of pH that yields \(N\&_\_H\)(AMP) is obtained as follows:

ampnhfun = calcavnoH[6.16, 3.71, 12];

These pKs in the ATP series were published by Alberty and Goldberg (3) in 1992.

The function of pH that yields \(\(N\&_\_H\) \((P\_i)\)\) is obtained as follows:

pinhfun = calcavnoH[6.65, 0, 1];

The second pK is set to zero to take it out of the calculation.

The function of pH that yields \(\(N\&_\_H\) \((adenosine)\)\) is obtained as follows:

adenosinenhfun = calcavnoH[3.47, 0, 13];

The function of pH that yields \(\(N\&_\_H\) \((\(H\_2\) O)\)\) is obtained as follows:

h2onhfun = calcavnoH[0, 0, 2];

Since water does not have a pK in the range pH 5 to 9, both pK1 and pK2 are set equal to zero.

The average numbers of hydrogen atoms in these six reactants are summarized in Table 1.

\(\(listnames = {"atp", "adp", "amp", "adenosine", "pi", "h2o"};\)\)

Table 1  Average numbers of hydrogen atoms \(N\&_\_H\) in six reactants at 298.15 K and 0.25 M ionic strength

PaddedForm[
      TableForm[{atpnhfun, adpnhfun, ampnhfun, adenosinenhfun, pinhfun, 
              h2onhfun} /. pH -> {5, 6, 7, 8, 9}, 
          TableHeadings -> {listnames, {"pH 5", "pH 6", "pH \
7", "pH 8", "pH 9"}}] // N, {4, 2}]

These numbers can be added and subtracted to obtain (Subscript[Δ, r]) (Subscript[N, H]) for a number of enzyme-catalyzed reactions, as shown in the next section.

3. Calculation of changes in binding of hydrogen ions in reactions involving the ATP series

This change is given by

(Subscript[Δ, r]) (Subscript[N, H]) = ∑(Subscript[ν, i])'\(N\&_\_H\) (i)													(10)

where (Subscript[ν, i])' is the stoichiometric number for reactant i.  This type of equation applies to (Subscript[Δ, r]) G' °, (Subscript[Δ, r]) H' °, and (Subscript[Δ, r]) S' °.  Therefore, correct stoichiometry for biochemical equations is very important.
	It is convenient to rewrite the program trGibbsRxSummary (inBasicBiochemData3.nb) to calculate (Subscript[Δ, r]) (Subscript[N, H]) for reactions that are typed in.  The program chgNHbindSummary does not require information on the standard Gibbs energies of formation of species.  The short program "round" rounds changes to two digits.  The names of reactants are those used in Mathematica where names have to start with lower case letters and connot contain dashes, spaces or periods.  The scientific names of reactants are given on p. 425 of Biochemical Thermodynamics: Applications of Mathematica (1).

round[vec_, params_:{6, 2}] :=(*When a list of numbers has more digits to the right of the decimal point than you want, say 6, you can request 2 by using round[vec,{6,2}],*) 
  Flatten[Map[NumberForm[#1, params] & , {vec}, {2}]]

chgNHbindSummary[eq_, title_, reaction_, pHlist_] := 
      Module[{functiom, 
          vectorNH},   
function = Solve[eq, de]; 
vectorNH = 
          round[function[[1, 1, 2]] /. pH -> pHlist, {4, 
              2}]; 
Print[title]; Print[reaction]; 
        Print[vectorNH]]

The following calculations give (Subscript[Δ, r]) (Subscript[N, H]) at pH 5, pH 6, pH 7, pH 8, and pH 9 at 298.15 K and 0.25 M ionic strength:

\(chgNHbindSummary[
      atpnhfun + h2onhfun + de == 
        adpnhfun + 
          pinhfun, "EC 3.6.1.3 Adenosinetriphosphatase", "atp+h2o=adp+pi", {5, 6, 7, 8, 9}]\)

This agrees with the entries in Chapters 12 and 13, but it was obtained without information on Gibbs energies of formation of species.

chgNHbindSummary[
      atpnhfun + 2*h2onhfun + de == 
        ampnhfun + 
          2*pinhfun, "EC 3.6.1.5 Apyrase", "atp+2*h2o=amp+2*pi", {5, 
        6, 7, 8, 9}]

The following reaction is not in Chapter 12.

\(chgNHbindSummary[
      adpnhfun + h2onhfun + de == 
        ampnhfun + 
          pinhfun, "EC 3.6.1.6 Nucleotide-diphosphatase reaction", "adp+h2o=amp+pi", {5, 6, 7, 8, 9}]\)

The following reaction is not in Chapter 12.

\(chgNHbindSummary[
      ampnhfun + h2onhfun + de == 
        adenosinenhfun + 
          pinhfun, "EC 3.1.3.1 Alkaline phosphatase reaction", "amp+h2o=adenosine+pi", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      atpnhfun + ampnhfun + de == 
        2*adpnhfun, "EC 2.7.4.3 Phosphotransferases with a phosphate group \
as acceptor", "atp+amp=2*adp", {5, 6, 7, 8, 9}]

This section has demonstrated that (Subscript[Δ, r]) (Subscript[N, H]) can be calculated from pKs and the number of hydrogen atoms in the most basic form of the reactant.  These are examples; now we can consider all the reactions in Chapter 12 of Biochemical Thermodynamics: Applications of Mathematica (1).

4. Derivation of the functions of pH that give the average numbers of hydrogen atoms in all the reactants in BasicBiochemData3.nb at 298.15 K and 0.25 M ionic strength

The functions for acetaldehydenhfun, etc., calculated in this section can be used to calculate \(N\&_\_H\) for 199 biochemical reactants and (Subscript[Δ, r]) (Subscript[N, H]) for 229 reactions that are treated in Chapter 12 of Biochemical Thermodynamics: Applications of Mathematica; see the next section.  For some reactants (Subscript[N, H]) (j) are relative.  For example, nHbasicform(CoA) = 0 and nHbasicform(acetylcoA)=3.

acetaldehydenhfun = calcavnoH[0, 0, 4];
acetatenhfun = calcavnoH[4.47, 0, 3];
acetoacetatenhfun = calcavnoH[0, 0, 5];
acetoacetylcoAnhfun = calcavnoH[0, 0, 5];
acetonenhfun = calcavnoH[0, 0, 6];
acetylcoAnhfun = calcavnoH[0, 0, 3];
acetylphosnhfun = calcavnoH[8.12, 4.83, 3];
aconitatecisnhfun = calcavnoH[0, 0, 3];
adeninenhfun = calcavnoH[4.20, 0, 5];
adenosinenhfun = calcavnoH[3.47, 0, 13];
adenosinephosphosulfatenhfun = calcavnoH[0, 0, 12];
adpnhfun = calcavnoH[6.33, 3.79, 12];
alaninenhfun = calcavnoH[0, 0, 7];
ammonianhfun = calcavnoH[9.25, 0, 3];
ampnhfun = calcavnoH[6.16, 3.71, 12];
arabinosenhfun = calcavnoH[0, 0, 10];
arabinose5phosnhfun = calcavnoH[6.12, 0, 9];
asparagineLnhfun = calcavnoH[0, 0, 8];
aspartatenhfun = calcavnoH[0, 0, 6];
atpnhfun = calcavnoH[6.47, 3.83, 12];
bpgnhfun = calcavnoH[6.83, 0, 4];
butanalnhfun = calcavnoH[0, 0, 8];
butanolnnhfun = calcavnoH[0, 0, 10];
butyratenhfun = calcavnoH[0, 0, 7];
cellobiosenhfun = calcavnoH[0, 0, 22];
citratenhfun = calcavnoH[5.54, 4.19, 5];
citrateisonhfun = calcavnoH[5.55, 4.15, 5];
co2gnhfun = calcavnoH[0, 0, 0];
co2totnhfun = calcavnoH[9.76, 6.08, 0];
coAnhfun = calcavnoH[8.10, 0, 0];
coAglutathionenhfun = calcavnoH[0, 0, 15];
coaqnhfun = calcavnoH[0, 0, 0];
cognhfun = calcavnoH[0, 0, 0];
creatinenhfun = calcavnoH[0, 0, 9];
creatininenhfun = calcavnoH[0, 0, 7];
cyclicampnhfun = calcavnoH[0, 0, 7];
cysteineLnhfun = calcavnoH[8.09, 0, 6];
cystineLnhfun = calcavnoH[0, 0, 12];
cytochromecoxnhfun = calcavnoH[0, 0, 0];
cytochromecrednhfun = calcavnoH[0, 0, 0];
cognhfun = calcavnoH[0, 0, 0];
deoxyadenosinenhfun = calcavnoH[3.47, 0, 13];
deoxyadpnhfun = calcavnoH[6.33, 3.79, 12];
deoxyampnhfun = calcavnoH[6.16, 3.71, 12];
deoxyatpnhfun = calcavnoH[6.47, 3.83, 12];
deoxyribosenhfun = calcavnoH[0, 0, 10];
deoxyribose1phosnhfun = calcavnoH[6.12, 0, 9];
deoxyribose5phosnhfun = calcavnoH[6.12, 0, 9];
dihydroxyacetonenhfun = calcavnoH[0, 0, 6];
dihydroxyacetonephosnhfun = calcavnoH[5.13, 0, 5];
ethanenhfun = calcavnoH[0, 0, 6];
ethanolnhfun = calcavnoH[0, 0, 6];
ethylacetatenhfun = calcavnoH[0, 0, 8];
fadenzoxnhfun = calcavnoH[0, 0, 31];
fadenzrednhfun = calcavnoH[0, 0, 33];
fadoxnhfun = calcavnoH[0, 0, 31];
fadrednhfun = calcavnoH[0, 0, 33];
ferredoxinoxnhfun = calcavnoH[0, 0, 0];
ferredoxinrednhfun = calcavnoH[0, 0, 0];
ferricnhfun = calcavnoH[0, 0, 0];
ferrousnhfun = calcavnoH[0, 0, 0];
fmnoxnhfun = calcavnoH[0, 0, 19];
fmnrednhfun = calcavnoH[0, 0, 21];
formatenhfun = calcavnoH[0, 0, 1];
fructosenhfun = calcavnoH[0, 0, 12];
fructose16phosnhfun = calcavnoH[5.52, 5.20, 10];
fructose6phosnhfun = calcavnoH[5.70, 0, 11];
fumaratenhfun = calcavnoH[4.03, 2.81, 2];
galactono14lactonenhfun = calcavnoH[0, 0, 10];
galactosenhfun = calcavnoH[0, 0, 12];
galactose1phosnhfun = calcavnoH[5.58, 0, 11];
galactose6phosnhfun = calcavnoH[5.58, 0, 11];
gluconolactonenhfun = calcavnoH[0, 0, 10];
gluconolactone6phosnhfun = calcavnoH[5.85, 0, 9];
glucosenhfun = calcavnoH[0, 0, 12];
glucose1phosnhfun = calcavnoH[5.93, 0, 11];
glucose6phosnhfun = calcavnoH[5.84, 0, 11];
glutamatenhfun = calcavnoH[0, 0, 8];
glutaminenhfun = calcavnoH[0, 0, 10];
glutathioneoxnhfun = calcavnoH[0, 0, 30];
glutathionerednhfun = calcavnoH[7.77, 0, 15];
glyceraldehydenhfun = calcavnoH[0, 0, 6];
glyceraldehydephosnhfun = calcavnoH[5.13, 0, 5];
glyceratenhfun = calcavnoH[0, 0, 5];
glycerolnhfun = calcavnoH[0, 0, 8];
glycerol3phosnhfun = calcavnoH[6.10, 0, 7];
glycinenhfun = calcavnoH[0, 0, 5];
glycolatenhfun = calcavnoH[0, 0, 3];
glycylglycinenhfun = calcavnoH[0, 0, 8];
glyoxylatenhfun = calcavnoH[0, 0, 1];
h2aqnhfun = calcavnoH[0, 0, 2];
h2gnhfun = calcavnoH[0, 0, 2];
h2onhfun = calcavnoH[0, 0, 2];
h2o2aqnhfun = calcavnoH[0, 0, 2];
h2saqnhfun = calcavnoH[12.35, 6.71, 0];
hydroxy2oxoglutaratenhfun = calcavnoH[0, 0, 4];
hydroxyglutaratenhfun = calcavnoH[0, 0, 6];
hydroxypropionatenhfun = calcavnoH[0, 0, 5];
hydroxypyruvatenhfun = calcavnoH[0, 0, 3];
hypoxanthinenhfun = calcavnoH[0, 0, 4];
i2crnhfun = calcavnoH[0, 0, 0];
iditolnhfun = calcavnoH[0, 0, 14];
idpnhfun = calcavnoH[8.43, 6.33, 10];
impnhfun = calcavnoH[8.78, 6.16, 10];
indolenhfun = calcavnoH[0, 0, 7];
inosinenhfun = calcavnoH[8.67, 0, 11];
iodideionnhfun = calcavnoH[0, 0, 0];
isomaltosenhfun = calcavnoH[0, 0, 22];
itpnhfun = calcavnoH[8.67, 6.47, 10];
ketoglutaramatenhfun = calcavnoH[0, 0, 5];
ketoglutaratenhfun = calcavnoH[0, 0, 4];
lactatenhfun = calcavnoH[0, 0, 5];
lactosenhfun = calcavnoH[0, 0, 22];
lactulosenhfun = calcavnoH[0, 0, 22];
leucineisoLnhfun = calcavnoH[0, 0, 13];
leucineLnhfun = calcavnoH[0, 0, 13];
lyxosenhfun = calcavnoH[0, 0, 10];
malatenhfun = calcavnoH[4.69, 0, 4];
maleatenhfun = calcavnoH[0, 0, 2];
maltosenhfun = calcavnoH[0, 0, 22];
malylcoAnhfun = calcavnoH[3.93, 0, 4];
mannitol1phosnhfun = calcavnoH[5.93, 0, 13];
mannitolDnhfun = calcavnoH[0, 0, 14];
mannosenhfun = calcavnoH[0, 0, 12];
mannose1phosnhfun = calcavnoH[5.87, 0, 11];
mannose6phosnhfun = calcavnoH[5.87, 0, 11];
methaneaqnhfun = calcavnoH[0, 0, 4];
methanegnhfun = calcavnoH[0, 0, 4];
methanolnhfun = calcavnoH[0, 0, 4];
methioninenhfun = calcavnoH[0, 0, 11];
methyl2oxopentanoatenhfun = calcavnoH[0, 0, 9];
methylmalatenhfun = calcavnoH[0, 0, 6];
methylmaleatenhfun = calcavnoH[5.70, 0, 4];
methylmalonylcoAnhfun = calcavnoH[3.93, 0, 4];
n2aqnhfun = calcavnoH[0, 0, 0];
n2gnhfun = calcavnoH[0, 0, 0];
n2oaqnhfun = calcavnoH[0, 0, 0];
nadoxnhfun = calcavnoH[0, 0, 26];
nadpoxnhfun = calcavnoH[0, 0, 25];
nadprednhfun = calcavnoH[0, 0, 26];
nadrednhfun = calcavnoH[0, 0, 27];
nicotinamideribonucleotidenhfun = calcavnoH[5.87, 0, 14];
nitratenhfun = calcavnoH[ .16, 0, 0];
nitritenhfun = calcavnoH[2.94, 0, 0];
noaqnhfun = calcavnoH[0, 0, 0];
o2aqnhfun = calcavnoH[0, 0, 0];
o2gnhfun = calcavnoH[0, 0, 0];
oxalatenhfun = calcavnoH[3.71, 0, 0];
oxaloacetatenhfun = calcavnoH[0, 0, 2];
oxalosuccinatenhfun = calcavnoH[0, 0, 4];
oxalylcoAnhfun = calcavnoH[0, 0, 0];
oxoprolinenhfun = calcavnoH[0, 0, 6];
palmitatenhfun = calcavnoH[0, 0, 31];
oxylatenhfun = calcavnoH[3.71, 0, 0];
pepnhfun = calcavnoH[6.15, 0, 2];
phenylalaninenhfun = calcavnoH[0, 0, 11];
phosphoglycerate2nhfun = calcavnoH[6.79, 0, 4];
phosphoglycerate3nhfun = calcavnoH[6.68, 0, 4];
phosphohydroxypyruvatenhfun = calcavnoH[0, 0, 2];
phosphoserinenhfun = calcavnoH[5.87, 0, 6];
pinhfun = calcavnoH[6.65, 0, 1];
ppinhfun = calcavnoH[8.33, 5.87, 0];
propanol2nhfun = calcavnoH[0, 0, 8];
propanolnnhfun = calcavnoH[0, 0, 8];
propanoylcoAnhfun = calcavnoH[0, 0, 5];
prppnhfun = calcavnoH[5.76, 5.56, 8];
pyruvatenhfun = calcavnoH[0, 0, 3];
retinalnhfun = calcavnoH[0, 0, 28];
retinolnhfun = calcavnoH[0, 0, 30];
ribitolnhfun = calcavnoH[0, 0, 12];
ribosenhfun = calcavnoH[0, 0, 10];
ribose1phosnhfun = calcavnoH[6.12, 0, 9];
ribose5phosnhfun = calcavnoH[6.12, 0, 9];
ribulosenhfun = calcavnoH[0, 0, 10];
ribulose5phosnhfun = calcavnoH[6.12, 0, 9];
serineLnhfun = calcavnoH[0, 0, 7];
sorbitolnhfun = calcavnoH[0, 0, 14];
sorbitol6phosnhfun = calcavnoH[5.85, 0, 13];
sorbosenhfun = calcavnoH[0, 0, 12];
succinatenhfun = calcavnoH[5.07, 3.92, 4];
succinylcoAnhfun = calcavnoH[3.92, 0, 4];
sucrosenhfun = calcavnoH[0, 0, 22];
sulfatenhfun = calcavnoH[1.42, 0, 0];
sulfitenhfun = calcavnoH[6.66, 0, 0];
sulfurcrnhfun = calcavnoH[0, 0, 0];
thioredoxinoxnhfun = calcavnoH[0, 0, 0];
thioredoxinrednhfun = calcavnoH[8.07, 7.76, 0];
threoninenhfun = calcavnoH[0, 0, 9];
transcinnamatenhfun = calcavnoH[0, 0, 7];
trehalosenhfun = calcavnoH[0, 0, 22];
tryptophanLnhfun = calcavnoH[0, 0, 12];
tyrosinenhfun = calcavnoH[0, 0, 11];
ubiquinoneoxnhfun = calcavnoH[0, 0, 90];
ubiquinonerednhfun = calcavnoH[0, 0, 92];
uratenhfun = calcavnoH[0, 0, 3];
ureanhfun = calcavnoH[0, 0, 4];
uricacidnhfun = calcavnoH[0, 0, 4];
valinenhfun = calcavnoH[0, 0, 11];
xylitolnhfun = calcavnoH[0, 0, 12];
xylosenhfun = calcavnoH[0, 0, 10];
xylulosenhfun = calcavnoH[0, 0, 10];

5. Calculation of changes in binding of hydrogen ions for 229 enzyme-catalyzed reactions that are treated at 298.15 K, 0.25 M ionic strength, and five pHs in Chapter 12 of Biochemical Thermodynamics: Applications of Mathematica

The functions of pH that give \(N\&_\_H\) for the 199 reactants in BasicBiochemData3.nb (2) at 298.15 K and 0.25 M ionic strength can be used to calculate the changes in binding of hydrogen ions for 229 reactions that are treated in Chapter 12 and more.  The following list of tables gives (Subscript[Δ, r])(Subscript[N, H]) at 298.15 K, 0.25 M ionic strength and pHs 5, 6, 7, 8, and 9.  The reactions are written in the direction for which K' > 1 at pH 7.

12.1 Oxidoreductase Reactions

EC 1.1  Acting on the CH-OH group of donors

\(chgNHbindSummary[
      acetaldehydenhfun + nadrednhfun + de == 
        ethanolnhfun + 
          nadoxnhfun, "EC 1.1.1.1a Alcohol dehydrogenase", "acetaldehyde+nadred=ethanol+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      butanalnhfun + nadrednhfun + de == 
        butanolnnhfun + 
          nadoxnhfun, "EC 1.1.1.1b Alcohol dehydrognase", "butanal+nadred=butanoln+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetonenhfun + nadrednhfun + de == 
        propanol2nhfun + 
          nadoxnhfun, "EC 1.1.1.1c Alcohol dehydrognase", "acetone+nadred=propanol2+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      dihydroxyacetonenhfun + nadrednhfun + de == 
        glycerolnhfun + 
          nadoxnhfun, "EC 1.1.1.6 Glycerol dehydrogenase", "dihydroxyacetone+nadred=glycerol+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      xylulosenhfun + nadprednhfun + de == 
        xylitolnhfun + 
          nadpoxnhfun, "EC 1.1.1.10 L-xylulose reductase", "xylulose+nadpred=xylitol+nadpox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      sorbosenhfun + nadrednhfun + de == 
        iditolnhfun + 
          nadoxnhfun, "EC 1.1.1.14 L-Iditol 2-dehydrognase", "sorbose+nadred=iditol+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      fructose6phosnhfun + nadrednhfun + de == 
        mannitol1phosnhfun + 
          nadoxnhfun, "EC 1.1.1.17 Mannitol-1-phosphate 5-dehydrogenase", "fructose6phos+nadred=mannitol1phos+nadox", {5, 6, 7, 8, 9}]\)

The small change in (Subscript[Δ, r]) (Subscript[N, H]) with pH is due to the small difference between pK1(fructose6phos) and pK1(mannitolphos).

\(chgNHbindSummary[
      glyoxylatenhfun + nadrednhfun + de == 
        glycolatenhfun + 
          nadoxnhfun, "EC 1.1.1.26 Glycolate reductase", "glyoxylate+nadred=glycolate+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pyruvatenhfun + nadrednhfun + de == 
        lactatenhfun + 
          nadoxnhfun, "EC 1.1.1.27 L-lactate dehydrogenase", "pyruvate+nadred=lactate+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      hydroxypyruvatenhfun + nadrednhfun + de == 
        glyceratenhfun + 
          nadoxnhfun, "EC 1.1.1.29 Glycerate dehydrogenase", "hydroxypyruvate+nadred=glycerate+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      oxaloacetatenhfun + nadrednhfun + de == 
        malatenhfun + 
          nadoxnhfun, "EC 1.1.1.37 Malate dehydrogenase", "oxaloacetate+nadred=malate+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pyruvatenhfun + nadrednhfun + co2totnhfun + de == 
        malatenhfun + nadoxnhfun + 
          h2onhfun, "EC 1.1.1.39 Malate dehydrogenase (decarboxylating)", "pyruvate+nadred+co2tot=malate+nadox+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      citrateisonhfun + nadpoxnhfun + h2onhfun + de == 
        ketoglutaratenhfun + nadprednhfun + 
          co2totnhfun, "EC 1.1.1.42 Isocitrate dehydrogenase (NADP)", "citrateiso+nadpox+h2o=ketoglutarate+nadpred+co2tot", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[\((galactosenhfun + nadoxnhfun + de == 
            galactono14lactonenhfun + nadrednhfun)\) // 
        N, "EC 1.1.1.48 Galactose 1-dehydrogenase", "galactose+nadox=galactono14lactone+nadred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucose6phosnhfun + nadpoxnhfun + de == 
        gluconolactone6phosnhfun + 
          nadprednhfun, "EC 1.1.1.49 Glucose-6-phosphate 1-dehydrogenase", "glucose6phos+nadpox=gluconolactone6phos+nadpred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((ribulosenhfun + nadrednhfun + de == 
            ribitolnhfun + nadoxnhfun)\) // 
        N, "EC 1.1.1.56 Ribitol 2-dehydrogenase", "ribulose+nadred=ribitol+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((fructosenhfun + nadrednhfun + de == 
            mannitolDnhfun + nadoxnhfun)\) // 
        N, "EC 1.1.1.67 Mannitol 2-dehydrogenase", "fructose+nadred=mannitolD+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glyceraldehydenhfun + nadprednhfun + de == 
        glycerolnhfun + 
          nadpoxnhfun, "EC 1.1.1.72 Glycerol dehydrogenase (NADP)", "glyceraldehyde+nadpred=glycerol+nadpox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glyoxylatenhfun + nadprednhfun + de == 
        glycolatenhfun + 
          nadpoxnhfun, "EC 1.1.1.79 Glyoxylate reductase (NADP)", "glyoxylate+nadpred=glycolate+nadpox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetonenhfun + nadprednhfun + de == 
        propanol2nhfun + 
          nadpoxnhfun, "EC 1.1.1.80 Isopropyl dehydrogenase (NADP)", "acetone+nadpred=propanol2+nadpox", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      dihydroxyacetonephosnhfun + nadprednhfun + de == 
        glycerol3phosnhfun + 
          nadpoxnhfun, "EC 1.1.1.94 Glycerol-3-phosphate dehydrogenase \
(NAD(P))", "dihydroxyacetonephos+nadpred=glycerol3phos+nadpox", {5, 6, 
        7, 8, 9}]

\(chgNHbindSummary[
      phosphohydroxypyruvatenhfun + nadrednhfun + de == 
        phosphoglycerate3nhfun + 
          nadoxnhfun, "EC 1.1.1.95 Phosphoglycerate dehydrogenase", "phosphohydroxypyruvate+nadred=phosphoglycerate3+nadox", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      retinalnhfun + nadrednhfun + de == 
        retinolnhfun + 
          nadoxnhfun, "EC 1.1.1.105 Retinol dehydrogenase", "retinal+nadred=retinol+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucosenhfun + nadpoxnhfun + de == 
        gluconolactonenhfun + 
          nadprednhfun, "EC 1.1.1.119 Glucose 1-dehydrogenase (NADP)", "glucose+nadpox=gluconolactone+nadpred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((fructosenhfun + nadprednhfun + de == 
            mannitolDnhfun + nadpoxnhfun)\) // 
        N, "EC 1.1.1.138 Mannitol 2-dehydrogenase (NADP)", "fructose+nadpred=mannitolD+nadpox", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      fructose6phosnhfun + nadrednhfun + de == 
        sorbitol6phosnhfun + 
          nadoxnhfun, "EC 1.1.1.140 Sorbitol-6-phosphate \
2-dehydrogenase", "fructose6phos+nadred=sorbitol6phos+nadox", {5, 6, 7, 
        8, 9}]

\(chgNHbindSummary[
      dihydroxyacetonenhfun + nadprednhfun + de == 
        glycerolnhfun + 
          nadpoxnhfun, "EC 1.1.1.156 Glycerol 2-dehydrogenase (NADP)", "dihydroxyacetone+nadpred=glycerol+nadpox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((mannitolDnhfun + cytochromecoxnhfun + de == 
            fructosenhfun + cytochromecrednhfun)\) // 
        N, "EC 1.1.2.2 Mannitol dehydrogenase (cytochrome)", "mannitolD+cytochromecox=fructose+cytochromecred", {5, 6, 7, 8, 
        9}]\)

chgNHbindSummary[
      lactatenhfun + 2*cytochromecoxnhfun + de == 
        pyruvatenhfun + 
          2*cytochromecrednhfun, "EC 1.1.2.3 L-Lactate dehydrogenase \
(cytochrome)", "lactate+2*cytochromecox=pyruvate+2*cytochromecred", {5, 
        6, 7, 8, 9}]

\(chgNHbindSummary[
      malatenhfun + o2aqnhfun + de == 
        oxaloacetatenhfun + 
          h2o2aqnhfun, "EC 1.1.3.3 Malate oxidase", "malate+o2aq=oxaloacetate+h2o2aq", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucosenhfun + o2aqnhfun + de == 
        gluconolactonenhfun + 
          h2o2aqnhfun, "EC 1.1.3.4 Glucose oxidase", "glucose+o2aq=gluconolactone+h2o2aq", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glycerol3phosnhfun + o2aqnhfun + de == 
        dihydroxyacetonephosnhfun + 
          h2o2aqnhfun, "EC 1.1.3.21 Glycerol-3-phosphate oxidase", "glycerol3phos+o2aq=dihydroxyacetonephos+h2o2aq", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[\((ketoglutaratenhfun + nadrednhfun + de == 
            hydroxyglutaratenhfun + nadoxnhfun)\) // 
        N, "EC 1.1.99.2 2-Hydroxyglutarate dehydrogenase", "ketoglutarate+nadred=hydroxyglutarate+nadox", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      lactatenhfun + oxaloacetatenhfun + de == 
        malatenhfun + 
          pyruvatenhfun, "EC 1.1.99.7 Lactate-malate trans-hydrogenase", "lactate+oxaloacetate=malate+pyruvate", {5, 6, 7, 8, 9}]\)

EC 1.2  Acting on the aldehyde or oxo group of donors

\(chgNHbindSummary[
      formatenhfun + nadoxnhfun + h2onhfun + de == 
        co2totnhfun + 
          nadrednhfun, "EC 1.2.1.2 Formate dehydrogenase", "formate+nadox+h2o=co2tot+nadred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetaldehydenhfun + nadoxnhfun + h2onhfun + de == 
        acetatenhfun + 
          nadrednhfun, "EC 1.2.1.3 Aldehyde dehydrogenase", "acetaldehyde+nadox+h2o=acetate+nadred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glyceraldehydephosnhfun + nadpoxnhfun + h2onhfun + de == 
        phosphoglycerate3nhfun + 
          nadprednhfun, "EC 1.2.1.9 Glyceraldehyde-3-phosphate dehydrogenase (NADP)", "glyceraldehydephos+nadpox+h2o=phosphoglycerate3+nadpred", {5, 6, 7, 8, 
        9}]\)

chgNHbindSummary[
      acetaldehydenhfun + coAnhfun + nadoxnhfun + de == 
        acetylcoAnhfun + 
          nadrednhfun, "EC 1.2.1.10 Acetaldehyde dehydrogenase \
(acetylating)", "acetaldehyde+coA+nadox=acetylcoA+nadred", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      formatenhfun + nadpoxnhfun + h2onhfun + de == 
        co2totnhfun + 
          nadprednhfun, "EC 1.2.1.43 Formate dehydrogenase (NADP)", "formate+nadpox+h2o=co2tot+nadpred", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      formatenhfun + cytochromecoxnhfun + h2onhfun + de == 
        co2totnhfun + 
          cytochromecrednhfun, "EC 1.2.2.3 Formate dehydrogenase \
(cytochrome)", "formate+cytochromecox+h2o=co2tot+cytochromecred", {5, 
        6, 7, 8, 9}]

\(chgNHbindSummary[
      coaqnhfun + 2*cytochromecoxnhfun + 2*h2onhfun + de == 
        co2totnhfun + 
          2*cytochromecrednhfun, "EC 1.2.2.4 Carbon-monoxide dehydrogenase (cytochrome)", "coaq+2*cytochromecox+2*h2o=co2tot+2*cytochromecred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pyruvatenhfun + pinhfun + o2aqnhfun + 2*h2onhfun + de == 
        acetylphosnhfun + co2totnhfun + 
          h2o2aqnhfun, "EC 1.2.3.3 Pyruvate oxidase", "pyruvate+pi+o2aq+2*h2o=acetylphos+co2tot+h2o2aq", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      oxalatenhfun + o2aqnhfun + 2*h2onhfun + de == 
        co2totnhfun + 
          h2o2aqnhfun, "EC 1.2.3.4 Oxalate oxidase", "oxalate+o2aq+2*h2o=co2tot+h2o2aq", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((glyoxylatenhfun + o2aqnhfun + h2onhfun + 
              de == oxalatenhfun + h2o2aqnhfun)\) // 
        N, "EC 1.2.3.5 Glyoxylate oxidase", "glyoxylate+o2aq+h2o=oxalate+h2o2aq", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      pyruvatenhfun + coAnhfun + o2aqnhfun + h2onhfun + de == 
        acetylcoAnhfun + co2totnhfun + 
          h2o2aqnhfun, "EC 1.2.3.6 Pyruvate oxidase (CoA-acetylating)", "\
pyruvate+coA+o2aq+h2o=acetylcoA+co2tot+h2o2aq", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      pyruvatenhfun + coAnhfun + ferredoxinoxnhfun + h2onhfun + de == 
        acetylcoAnhfun + co2totnhfun + 
          ferredoxinrednhfun, "EC 1.2.7.1 Pyruvate synthase", "pyruvate+coA+ferredoxinox+h2o=acetylcoA+co2tot+ferredoxinred", {5, 6, 7, 
        8, 9}]\)

EC 1.4  Acting on the CH-NH(2) group  of donors

\(chgNHbindSummary[
      pyruvatenhfun + nadrednhfun + ammonianhfun + de == 
        alaninenhfun + nadoxnhfun + 
          h2onhfun, "EC 1.4.1.1 Alanine dehydrogenase", "pyruvate+nadred+ammonia=alanine+nadox+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ketoglutaratenhfun + nadrednhfun + ammonianhfun + de == 
        glutamatenhfun + nadoxnhfun + 
          h2onhfun, "EC 1.4.1.2 Glutamate dehydrogenase", "ketoglutarate+nadred+ammonia=glutamate+nadox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      ketoglutaratenhfun + nadprednhfun + ammonianhfun + de == 
        glutamatenhfun + nadpoxnhfun + 
          h2onhfun, "EC 1.4.1.3 Glutamate dehydrogenase (NAD(P))", "ketoglutarate+nadpred+ammonia=glutamate+nadpox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      hydroxypyruvatenhfun + nadrednhfun + ammonianhfun + de == 
        serineLnhfun + nadoxnhfun + 
          h2onhfun, "EC 1.4.1.7 Serine 2-dehydrogenase", "hydroxypyruvate+nadred+ammonia=serineL+nadox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      methyl2oxopentanoatenhfun + nadrednhfun + ammonianhfun + de == 
        leucineLnhfun + nadoxnhfun + 
          h2onhfun, "EC 1.4.1.9 Leucine dehydrogenase", "methyl2oxopentanoate+nadred+ammonia=leucineL+nadox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      glyoxylatenhfun + nadrednhfun + ammonianhfun + de == 
        glycinenhfun + nadoxnhfun + 
          h2onhfun, "EC 1.4.1.10 Glycine dehydrogenase", "glyoxylate+nadred+ammonia=glycine+nadox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      glycinenhfun + h2onhfun + 2*cytochromecoxnhfun + de == 
        glyoxylatenhfun + ammonianhfun + 
          2*cytochromecrednhfun, "EC 1.4.2.1 Glycine dehydrogenase (cytochrome)", "glycine+h2o+2*cytochromecox=glyoxylate+ammonia+2*cytochromecred", {5, 6, 
        7, 8, 9}]\)

\(chgNHbindSummary[
      glutamatenhfun + o2aqnhfun + h2onhfun + de == 
        ketoglutaratenhfun + ammonianhfun + 
          h2o2aqnhfun, "EC 1.4.3.11 L-Glutamate oxidase", "glutamate+o2aq+h2o=ketoglutarate+ammonia+h2o2aq", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      aspartatenhfun + o2aqnhfun + h2onhfun + de == 
        oxaloacetatenhfun + ammonianhfun + 
          h2o2aqnhfun, "EC 1.4.3.16 L-Aspartate oxidase", "aspartate+o2aq+h2o=oxaloacetate+ammonia+h2o2aq", {5, 6, 7, 8, 
        9}]\)

EC 1.5  Acting on NADH or NADPH

\(chgNHbindSummary[
      nadprednhfun + fmnoxnhfun + de == 
        nadpoxnhfun + 
          fmnrednhfun, "EC 1.5.1.29 FMN reductase", "nadpred+fmnox=nadpox+fmnred", {5, 6, 7, 8, 9}]\)

EC 1.6  Acting on (Subscript[NAD, red]) or (Subscript[NADP, red])

\(chgNHbindSummary[
      nadpoxnhfun + nadrednhfun + de == 
        nadprednhfun + 
          nadoxnhfun, "EC 1.6.1.1 NAD(P) transhydrogenase", "nadpox+nadred=nadpred+nadox", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      nadprednhfun + 2*cytochromecoxnhfun + de == 
        nadpoxnhfun + 
          2*cytochromecrednhfun, "EC 1.6.2.5 NAD(P)-cytochromec \
reductase", "nadpred+2*cytochromecox=nadpox+2*cytochromecred", {5, 6, 
        7, 8, 9}]

chgNHbindSummary[
      nadrednhfun + ubiquinoneoxnhfun + de == 
        nadoxnhfun + 
          ubiquinonerednhfun, "EC 1.6.5.3 NADH dehydrogenase \
(ubiquinone)", "nadred+ubiquinoneox=nadox+ubiquinonered", {5, 6, 7, 8, 
        9}]

EC 1.7  Acting on other nitrogenous compounds as donors

\(chgNHbindSummary[
      nadrednhfun + nitratenhfun + de == 
        nadoxnhfun + nitritenhfun + 
          h2onhfun, "EC 1.7.1.1 Nitrate reductase (NADH)", "nadred+nitrate=nadox+nitrite+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      nadprednhfun + nitratenhfun + de == 
        nadpoxnhfun + nitritenhfun + 
          h2onhfun, "EC 1.7.1.3 Nitrate reductase (NADP)", "nadpred+nitrate=nadpox+nitrite+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      nitritenhfun + 3*nadprednhfun + de == 
        ammonianhfun + 3*nadpoxnhfun + 
          2*h2onhfun, "EC 1.7.1.4 Nitrite reductase (NADP)", "nitrite+3*nadpred=ammonia+3*nadpox+2*h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      nitritenhfun + cytochromecrednhfun + de == 
        noaqnhfun + cytochromecoxnhfun + 
          h2onhfun, "EC 1.7.2.1 Nitrite reductase (NO forming)", "nitrite+cytochromecred=noaq+cytochromecox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      nitritenhfun + 6*cytochromecrednhfun + de == 
        ammonianhfun + 6*cytochromecoxnhfun + 
          2*h2onhfun, "EC 1.7.2.2 Nitrite reductase (cytochrome, ammonia forming)", "nitrite+6*cytochromecred=ammonia+6*cytochromecox+2*h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      nitritenhfun + 3*ferredoxinrednhfun + de == 
        ammonianhfun + 3*ferredoxinoxnhfun + 
          2*h2onhfun, "EC 1.7.7.1 Ferredoxin-nitrite reductase", "nitrite+3*ferredoxinred=ammonia+3*ferredoxinox+2*h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      nitratenhfun + 2*ferredoxinrednhfun + de == 
        nitritenhfun + h2onhfun + 
          2*ferredoxinoxnhfun, "EC 1.7.7.2 Ferredoxin-nitrate reductase", "nitrate+2*ferredoxinred=nitrite+h2o+2*ferredoxinox", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      n2oaqnhfun + nadrednhfun + de == 
        n2aqnhfun + 
          nadoxnhfun, "EC 1.7.99.6 Nitrous oxide reductase", "n2oaq+nadred=n2aq+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((2*noaqnhfun + nadrednhfun + de == 
            n2oaqnhfun + nadoxnhfun)\) // 
        N, "EC 1.7.99.7 Nitric oxide reductase", "2*noaq+nadred=n2oaq+nadox", {5, 6, 7, 8, 9}]\)

EC 1.8  Acting on a sulfur group of donors

\(chgNHbindSummary[
      sulfitenhfun + 3*nadprednhfun + de == 
        h2saqnhfun + 3*nadpoxnhfun + 
          3*h2onhfun, "EC 1.8.1.2 Sulfite reductase", "sulfite+3*nadpred=h2saq+3*nadpox+3*h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      2*cysteineLnhfun + nadoxnhfun + de == 
        cystineLnhfun + 
          nadrednhfun, "EC 1.8.1.6 Cystine reductase", "2*cysteineL+nadox=cystineL+nadred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glutathioneoxnhfun + nadprednhfun + de == 
        2*glutathionerednhfun + 
          nadpoxnhfun, "EC 1.8.1.7 Glutathione reductase (NADP)", "glutathioneox+nadpred=2*glutathionered+nadpox", {5, 6, 7, 8, 
        9}]\)

chgNHbindSummary[
      thioredoxinoxnhfun + nadprednhfun + de == 
        thioredoxinrednhfun + 
          nadpoxnhfun, "EC 1.8.1.9 Thioredoxin-disulfide reductase \
(NADP)", "thioredoxinox+nadpredthioredoxinred+nadpox", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      coAglutathionenhfun + nadprednhfun + de == 
        coAnhfun + glutathionerednhfun + 
          nadpoxnhfun, "EC 1.8.1.10 CoA-glutathione reductase (NADP)", "coAglutathione+nadpred=coA+glutathionered+nadpox", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      sulfitenhfun + 2*cytochromecoxnhfun + h2onhfun + de == 
        sulfatenhfun + 
          2*cytochromecrednhfun, "EC 1.8.2.1 Sulfite dehydrogenase", "sulfite+2*cytochromecox+h2o=sulfate+2*cytochromecred", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      sulfitenhfun + o2aqnhfun + h2onhfun + de == 
        sulfatenhfun + 
          h2o2aqnhfun, "EC 1.8.3.1 Sulfite oxidase", "sulfite+o2aq+h2o=sulfate+h2o2aq", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      2*glutathionerednhfun + o2aqnhfun + de == 
        glutathioneoxnhfun + 
          h2o2aqnhfun, "EC 1.8.3.3 Glutathione oxidase", "2*glutathionered+o2aq=glutathioneox+h2o2aq", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glutathioneoxnhfun + 2*cysteineLnhfun + de == 
        2*glutathionerednhfun + 
          cystineLnhfun, "EC 1.8.4.4 Glutathione-cystine transhydrogenase", "glutathioneox+2*cysteineL=2*glutathionered+cystineL", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      sulfitenhfun + 6*ferredoxinrednhfun + de == 
        h2saqnhfun + 6*ferredoxinoxnhfun + 
          3*h2onhfun, "EC 1.8.7.1 Sulfite reductase (ferredoxin)", "sulfite+6*ferredoxinred=h2saq+6*ferredoxinox+3*h2o", {5, 6, 7, 8, 
        9}]\)

EC 1.9  Acting on a heme group of donors

\(chgNHbindSummary[\((4*cytochromecrednhfun + o2aqnhfun + de == 
            4*cytochromecoxnhfun + 2*h2onhfun)\) // 
        N, "EC 1.9.3.1 Cytochrome-c oxidase", "4*cytochromecred+o2aq=4*cytochromecox+2*h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      nitratenhfun + 2*cytochromecrednhfun + 
          de == 
nitritenhfun + 
          2*cytochromecoxnhfun + 
          h2onhfun, "EC 1.9.6.1 Nitrate reductase (cytochrome)", "nitrate+2*cytochromecred=nitrite+2*cytochromecox+h2o", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      ferricnhfun + cytochromecrednhfun + de == 
        ferrousnhfun + 
          cytochromecoxnhfun, "EC 1.9.99.1 Iron-cytochrome-c reductase", "ferric+cytochromecred=ferrous+cytochromecox", {5, 6, 7, 8, 
        9}]\)

EC 1.11 Acting on a peroxide as acceptor

\(chgNHbindSummary[\((nadrednhfun + h2o2aqnhfun + de == 
            nadoxnhfun + 2*h2onhfun)\) // 
        N, "EC 1.11.1.1 NADH peroxidase", "nadred+h2o2aq=nadox+2*h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((2*cytochromecrednhfun + h2o2aqnhfun + de == 
            2*cytochromecoxnhfun + 2*h2onhfun)\) // 
        N, "EC 1.11.1.5 Cytochromec peroxidase", "2*cytochromecred+h2o2aq=2*cytochromecox+2*h2o", {5, 6, 7, 8, 
        9}]\)

chgNHbindSummary[(2*h2o2aqnhfun + de == 
            o2aqnhfun + 2*h2onhfun) // 
        N, "EC 1.11.1.6 Catalase", "2*h2o2aq=o2aq+2*h2o", {5, 6, 7, 
        8, 9}]

\(chgNHbindSummary[
      2*iodideionnhfun + h2o2aqnhfun + de == 
        i2crnhfun + 
          2*h2onhfun, "EC 1.11.1.8 Iodide peroxidase", "2*iodideion+h2o2aq=i2cr+2*h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      2*glutathionerednhfun + h2o2aqnhfun + de == 
        glutathioneoxnhfun + 
          2*h2onhfun, "EC 1.11.1.9 Glutathione peroxidase", "2*glutathionered+h2o2aq=glutathioneox+2*h2o", {5, 6, 7, 8, 
        9}]\)

EC 1.12  Acting on hydrogen as donor

\(chgNHbindSummary[\((h2aqnhfun + nadoxnhfun + de == nadrednhfun)\) // 
        N, "EC 1.12.1.2 Hydrogen hydrogenase", "h2aq+nadox=nadred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[ .5*h2aqnhfun + cytochromecoxnhfun + de == 
        cytochromecrednhfun, "EC 1.12.2.1 Cytochrome-c hydrogenase", ".5*h2aq+cytochromecox=cytochromecred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((2*ferredoxinoxnhfun + h2aqnhfun + de == 
            2*ferredoxinrednhfun)\) // 
        N, "EC 1.18.99.1 Hydrogenase", "2*ferredoxinox+h2aq=2*ferredoxinred", {5, 6, 7, 8, 9}]\)

EC 1.13  Acting on single donors with incorporation of molecular oxygen

\(chgNHbindSummary[
      sulfurcrnhfun + o2aqnhfun + h2onhfun + de == 
        sulfitenhfun, "EC 1.13.1.18 Sulfur dioxygenase", "sulfurcr+o2aq+h2o=sulfite", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      lactatenhfun + o2aqnhfun + de == 
        acetatenhfun + 
          co2totnhfun, "EC 1.13.12.4 Lactate 2-monooxygenase", "lactate+o2aq=acetate+co2tot", {5, 6, 7, 8, 9}]\)

Note no h2o.

EC 1.14  Acting on paired donors, with incorporation or reduction

\(chgNHbindSummary[
      methaneaqnhfun + nadprednhfun + o2aqnhfun + de == 
        methanolnhfun + nadpoxnhfun + 
          h2onhfun, "EC 1.14.13.25 Methane monooxygenase", "methaneaq+nadpred+o2aq=methanol+nadpox+h2o", {5, 6, 7, 8, 9}]\)

EC 1.16  Oxidizing metal ions

\(chgNHbindSummary[
      2*ferricnhfun + nadrednhfun + de == 
        2*ferrousnhfun + 
          nadoxnhfun, "EC 1.16.1.7 Ferric chelate reductase", "2*ferric+nadred=2*ferrous+nadox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((4*ferrousnhfun + o2aqnhfun + de == 
            4*ferricnhfun + 2*h2onhfun)\) // 
        N, "EC 1.16.3.1 Ferrioxidase", "4*ferrous+o2aq=4*ferric+2*h2o", {5, 6, 7, 8, 9}]\)

EC 1.18  Acting on iron-sulfur proteins as donors

\(chgNHbindSummary[
      ferredoxinoxnhfun + nadprednhfun + de == 
        ferredoxinrednhfun + 
          nadpoxnhfun, "EC 1.18.1.2 Ferredoxin-NADP reductase", "ferredoxinox+nadpred=ferredoxinred+nadpox", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      n2aqnhfun + 8*ferredoxinrednhfun + 16*atpnhfun + 16*h2onhfun + 
          de == 
        2*ammonianhfun + h2aqnhfun + 8*ferredoxinoxnhfun + 16*adpnhfun + 
          16*pinhfun, "EC 1.18.6.1 Nitrogenase", "n2aq+8*ferredoxinred+16*atp+16*h2o=2*ammonia+h2aq+8*ferredoxinox+16*adp+16*pi", {5, 6, 7, 8, 9}]\)

12.2  Transferase Reactions

EC 2.1  Transferring one-carbon groups

chgNHbindSummary[
      methylmalonylcoAnhfun + pyruvatenhfun + de == 
        propanoylcoAnhfun + 
          oxaloacetatenhfun, "EC 2.1.3.1 Methylmalonyl-CoA \
carboxytransferase", "methylmalonylcoA+pyruvate=propanoylcoA+oxaloacetate\
", {5, 6, 7, 8, 9}]

EC 2.3  Acyltransferases

\(chgNHbindSummary[
      coAnhfun + acetylphosnhfun + de == 
        acetylcoAnhfun + 
          pinhfun, "EC 2.3.1.8 Phosphate acetyltransferase", "coA+acetylphos=acetylcoA+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      coAnhfun + acetoacetylcoAnhfun + de == 
        2*acetylcoAnhfun, "EC 2.3.1.9 Acetyl-CoA C-acetyltransferase", "coA+acetoacetylcoA+de==2*acetylcoA", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      coAnhfun + pyruvatenhfun + de == 
        acetylcoAnhfun + 
          formatenhfun, "EC 2.3.1.54 Formate C-acetyltransferase", "coA+pyruvate=acetylcoA+formate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetylcoAnhfun + h2onhfun + oxaloacetatenhfun + de == 
        coAnhfun + 
          citratenhfun, "EC 2.3.3.1 Citrate synthase", "acetylcoA+h2o+oxaloacetate=coA+citrate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adpnhfun + pinhfun + acetylcoAnhfun + oxaloacetatenhfun + de == 
        atpnhfun + citratenhfun + 
          coAnhfun, "EC 2.3.3.8 ATP citrate synthase", "adp+pi+acetylcoA+oxaloacetate=atp+citrate+coA", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      acetylcoAnhfun + h2onhfun + glyoxylatenhfun + de == 
        coAnhfun + 
          malatenhfun, "EC 2.3.3.9 Malate synthase", "acetylcoA+h2o+glyoxylate=coA+malate", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      propanoylcoAnhfun + h2onhfun + glyoxylatenhfun + de == 
        coAnhfun + 
          hydroxyglutaratenhfun, "EC 2.3.3.11 2-Hydroxyglutarate \
synthase", "propanoylcoA+h2o+glyoxylate=coA+hydroxyglutarate", {5, 6, 
        7, 8, 9}]

EC 2.4  Glycosyltransferases

\(chgNHbindSummary[
      sucrosenhfun + pinhfun + de == 
        fructosenhfun + 
          glucose6phosnhfun, "EC 2.4.1.7 Sucrose phosphorylase", "sucrose+pi=fructose+glucose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      maltosenhfun + pinhfun + de == 
        glucosenhfun + 
          glucose1phosnhfun, "EC 2.4.1.8 Maltose phosphorylase", "maltose+pi=glucose+glucose1phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucosenhfun + glucose1phosnhfun + de == 
        cellobiosenhfun + 
          pinhfun, "EC 2.4.1.20 Cellosebiose phosphorylase", "glucose+glucose1phos=cellobiose+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      2*glucose1phosnhfun + de == 
        maltosenhfun + 
          2*pinhfun, "EC 2.4.1.39 Maltose synthase", "2*glucose1phos=maltose+2*pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adeninenhfun + ribose1phosnhfun + de == 
        adenosinenhfun + 
          pinhfun, "EC 2.4.2.1 Purine-nucleoside phosphorylase", "adenine+ribose1phos=adenosine+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adeninenhfun + prppnhfun + de == 
        ampnhfun + 
          ppinhfun, "EC 2.4.2.7 Adenine phosphoribosyltransferase", "adenine+prpp=amp+ppi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      hypoxanthinenhfun + prppnhfun + de == 
        impnhfun + 
          ppinhfun, "EC 2.4.2.8 Hypoxanthine phosphoribosyltransferase", "hypoxanthine+prpp=imp+ppi", {5, 6, 7, 8, 9}]\)

EC 2.6  Transferring nitrogenous groups

\(chgNHbindSummary[
      aspartatenhfun + ketoglutaratenhfun + de == 
        oxaloacetatenhfun + 
          glutamatenhfun, "EC 2.6.1.1 Aspartate transaminase", "aspartate+ketoglutarate=oxaloacetate+glutamate", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      alaninenhfun + ketoglutaratenhfun + de == 
        pyruvatenhfun + 
          glutamatenhfun, "EC 2.6.1.2 Alanine transaminase", "alanine+ketoglutarate=pyruvate+glutamate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glyoxylatenhfun + glutamatenhfun + de == 
        glycinenhfun + 
          ketoglutaratenhfun, "EC 2.6.1.4 Glycine transaminase", "glyoxylate+glutamate=glycine+ketoglutarate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      methyl2oxopentanoatenhfun + glutamatenhfun + de == 
        leucineLnhfun + 
          ketoglutaratenhfun, "EC 2.6.1.6 Leucine transaminase", "methyl2oxopentanoate+glutamate=leucineL+ketoglutarate", {5, 6, 7, 8, 
        9}]\)

chgNHbindSummary[
      glyoxylatenhfun + aspartatenhfun + de == 
        glycinenhfun + 
          oxaloacetatenhfun, "EC 2.6.1.35 Glycine-oxaloacetate transaminase\
", "glyoxylate+aspartate=glycine+oxaloacetate", {5, 6, 7, 8, 
        9}]

chgNHbindSummary[
      alaninenhfun + glyoxylatenhfun + de == 
        glycinenhfun + 
          pyruvatenhfun, "EC 2.6.1.44 Alanine-glyoxylate transaminase", "\
alanine+glyoxylate=glycine+pyruvate", {5, 6, 7, 8, 9}]

chgNHbindSummary[
      serineLnhfun + glyoxylatenhfun + de == 
        glycinenhfun + 
          hydroxypyruvatenhfun, "EC 2.6.1.45 Serine-glyoxylate transaminase\
", "serineL+glyoxylate=glycine+hydroxypyruvate", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      alaninenhfun + hydroxypyruvatenhfun + de == 
        serineLnhfun + 
          pyruvatenhfun, "EC 2.6.1.51 Serine-pyruvate transaminase", "alanine+hydroxypyruvate=serineL+pyruvate", {5, 6, 7, 8, 9}]\)

EC 2.7  Transferring phosphorous-containing groups

\(chgNHbindSummary[
      atpnhfun + glucosenhfun + de == 
        adpnhfun + 
          glucose6phosnhfun, "EC 2.7.1.2 Glucokinase", "atp+glucose=adp+glucose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + fructosenhfun + de == 
        adpnhfun + 
          fructose6phosnhfun, "EC 2.7.1.4 Fructokinase", "atp+fructose=adp+fructose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + galactosenhfun + de == 
        adpnhfun + 
          galactose1phosnhfun, "EC 2.7.1.6 Galactokinase", "atp+galactose=adp+galactose1phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + mannosenhfun + de == 
        adpnhfun + 
          mannose6phosnhfun, "EC 2.7.1.7 Mannokinase", "atp+mannose=adp+mannose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + fructose6phosnhfun + de == 
        adpnhfun + 
          fructose16phosnhfun, "EC 2.7.1.11 6-phosphofructokinase", "atp+fructose6phos=adp+fructose16phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + ribosenhfun + de == 
        adpnhfun + 
          ribose5phosnhfun, "EC 2.7.1.15 Ribokinase", "atp+ribose=adp+ribose5phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + adenosinenhfun + de == 
        adpnhfun + 
          ampnhfun, "EC 2.7.1.20 Adenosine kinase", "atp+adenosine=adp+amp", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + nadoxnhfun + de == 
        adpnhfun + 
          nadpoxnhfun, \*""EC 2.7.1.23 (Subscript[NAD, ox]) kinase"", "atp+nadox=adp+nadpox", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      atpnhfun + dihydroxyacetonenhfun + de == 
        adpnhfun + 
          dihydroxyacetonephosnhfun, "EC 2.7.1.29 Dihydroxyacetone \
kinase", "atp+dihydroxyacetone=adp+dihydroxyacetonephos", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      atpnhfun + glycerolnhfun + de == 
        adpnhfun + 
          glycerol3phosnhfun, "EC 2.7.1.30 Glycerole kinase", "atp+glycerol=adp+glycerol3phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + glyceratenhfun + de == 
        adpnhfun + 
          phosphoglycerate3nhfun, "EC 2.7.1.31 Glycerate kinase", "atp+glycerate=adp+phosphoglycerate3", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adpnhfun + pepnhfun + de == 
        atpnhfun + 
          pyruvatenhfun, "EC 2.7.1.40 Pyruvate kinase", "adp+pep=atp+pyruvate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + ribulosenhfun + de == 
        adpnhfun + 
          ribulose5phosnhfun, "EC 2.7.1.47 D-ribulokinase", "atp+ribulose=adp+ribulose5phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + arabinosenhfun + de == 
        adpnhfun + 
          arabinose5phosnhfun, "EC 2.7.1.54 D-arabinosekinase", "atp+arabinose=adp+arabinose5phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + inosinenhfun + de == 
        adpnhfun + 
          impnhfun, "EC 2.7.1.73 Inosine kinase", "atp+inosine=adp+imp", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + deoxyadenosinenhfun + de == 
        adpnhfun + 
          deoxyampnhfun, "EC 2.7.1.76 Deoxyadenosine kinase", "atp+deoxyadenosine=adp+deoxyamp", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      ppinhfun + serineLnhfun + de == 
        pinhfun + 
          phosphoserinenhfun, "EC 2.7.1.80 Diphosphate-serine \
phosphotransferase", "ppi+serineL=pi+phosphoserine", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      atpnhfun + nadrednhfun + de == 
        adpnhfun + 
          nadprednhfun, \*""EC 2.7.1.86 (Subscript[NAD, red]) kinase"", "atp+nadred=adp+nadpred", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ppinhfun + fructose6phosnhfun + de == 
        pinhfun + 
          fructose16phosnhfun, "EC 2.7.1.90 Diphosphate-fructose-6-phosphate 1-phosphotransferase", "ppi+fructose6phos=pi+fructose16phos", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      glycerolnhfun + glucose6phosnhfun + de == 
        glycerol3phosnhfun + 
          glucosenhfun, "EC 2.7.1.142 Glycerol-3-phosphate-glucose \
phosphotransferase", "glycerol+glucose6phos=glycerol3phos+glucose", {5, 
        6, 7, 8, 9}]

chgNHbindSummary[
      adpnhfun + fructose6phosnhfun + de == 
        ampnhfun + 
          fructose16phosnhfun, "EC 2.7.1.146 ADP-specfic \
phosphofructokinase", "adp+fructose6phos=amp+fructose16phos", {5, 6, 7, 
        8, 9}]

\(chgNHbindSummary[
      adpnhfun + glucosenhfun + de == 
        ampnhfun + 
          glucose6phosnhfun, "EC 2.7.1.147 ADP-specific glucokinase", "adp+glucose=amp+glucose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adpnhfun + acetylphosnhfun + de == 
        atpnhfun + 
          acetatenhfun, "EC 2.7.2.1 Acetate kinase", "adp+acetylphos=atp+acetate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pinhfun + acetylphosnhfun + de == 
        ppinhfun + 
          acetatenhfun, "EC 2.7.2.12 Acetate kinase (diphosphate)", "pi+acetylphos=ppi+acetate", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      atpnhfun + ampnhfun + de == 
        2*adpnhfun, "EC 2.7.4.3 Phosphotransferases with a phosphate group \
as acceptor", "atp+amp=2*adp", {5, 6, 7, 8, 9}]

\(chgNHbindSummary[
      atpnhfun + ribose5phosnhfun + de == 
        ampnhfun + 
          prppnhfun, "EC 2.7.6.1 Ribose-phosphate diphosphokinase", "atp+ribose5phos=amp+prpp", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ppinhfun + nadoxnhfun + de == 
        atpnhfun + 
          nicotinamideribonucleotidenhfun, "EC 2.7.7.1 nicotinamide-nucleotide adenylyltransferase", "ppi+nadox=atp+nicotinamideribonucleotide", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ppinhfun + adenosinephosphosulfatenhfun + de == 
        atpnhfun + 
          sulfatenhfun, "EC 2.7.7.4 Sulfate adenylyltransferase", "ppi+adenosinephosphosulfate=atp+sulfate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ampnhfun + pepnhfun + ppinhfun + de == 
        atpnhfun + pyruvatenhfun + 
          pinhfun, "EC 2.7.9.1 Pyruvate,phosphate dikinase", "amp+pep+ppi=atp+pyruvate+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + pyruvatenhfun + h2onhfun + de == 
        ampnhfun + pepnhfun + 
          pinhfun, "EC 2.7.9.2 Pyruvate,water dikinase", "atp+pyruvate+h2o=amp+pep+pi", {5, 6, 7, 8, 9}]\)

12.3  Hydrolase Reactions

EC 3.1  Acting on ester bonds

\(chgNHbindSummary[
      ethylacetatenhfun + h2onhfun + de == 
        ethanolnhfun + 
          acetatenhfun, "EC 3.1.1.1 Carboxylesterase", "ethylacetate+h2o=ethanol+acetate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetylcoAnhfun + h2onhfun + de == 
        coAnhfun + 
          acetatenhfun, "EC 3.1.2.1 Acetyl-CoA hydrolase", "acetylcoA+h2o=coA+acetate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      succinylcoAnhfun + h2onhfun + de == 
        coAnhfun + 
          succinatenhfun, "EC 3.1.2.3 Succinyl-CoA hydrolase", "succinylcoA+h2o=coA+succinate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetoacetylcoAnhfun + h2onhfun + de == 
        coAnhfun + 
          acetoacetatenhfun, "EC 3.1.2.11 Acetoacetyl-CoA hydrolase", "acetoacetylcoA+h2o=coA+acetoacetate", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      oxalylcoAnhfun + h2onhfun + de == 
        coAnhfun + 
          oxalatenhfun, "EC 3.1.2.18 ADP-dependent short-chain-acyl-CoA \
hydrolase", "oxalylcoA+h2o=coA+oxalate", {5, 6, 7, 8, 9}]

\(chgNHbindSummary[
      phosphoserinenhfun + h2onhfun + de == 
        serineLnhfun + 
          pinhfun, "EC 3.1.3.3 Phosphoserine phosphatase", "phosphoserine+h2o=serineL+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucose6phosnhfun + h2onhfun + de == 
        glucosenhfun + 
          pinhfun, "EC 3.1.3.9 Glucose-6-phosphatase", "glucose6phos+h2o=glucose+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glucose1phosnhfun + h2onhfun + de == 
        glucosenhfun + 
          pinhfun, "EC 3.1.3.10 Glucose-1-phosphatase", "glucose1phos+h2o=glucose+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      fructose16phosnhfun + h2onhfun + de == 
        fructose6phosnhfun + 
          pinhfun, "EC 3.1.3.11 Fructose-bisphosphatase", "fructose16phos+h2o=fructose6phos+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      bpgnhfun + h2onhfun + de == 
        phosphoglycerate3nhfun + 
          pinhfun, "EC 3.1.3.13 Bisphosphoglycerate phosphatase", "bpg+h2o=phosphoglycerate3+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glycerolnhfun + pinhfun + de == 
        glycerol3phosnhfun + 
          h2onhfun, "EC 3.1.3.31 Nucleotidase", "glycerol+pi=glycerol3phos+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      phosphoglycerate3nhfun + h2onhfun + de == 
        glyceratenhfun + 
          pinhfun, "EC 3.1.3.38 3-phosphoglycerate phosphatase", "phosphoglycerate3+h2o=glycerate+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      sorbitol6phosnhfun + h2onhfun + de == 
        sorbitolnhfun + 
          pinhfun, "EC 3.1.3.50 Sorbitol-6-phosphatase", "sorbitol6phos+h2o=sorbitol+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pepnhfun + h2onhfun + de == 
        pyruvatenhfun + 
          pinhfun, "EC 3.1.3.60 Phosphoenolpyruvate phosphatase", "pep+h2o=pyruvate+pi", {5, 6, 7, 8, 9}]\)

EC 3.2  Glycosylases

\(chgNHbindSummary[
      maltosenhfun + h2onhfun + de == 
        2*glucosenhfun, "EC 3.2.1.20 Alpha-glucosidase", "maltose+h2o=2*glucose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      sucrosenhfun + h2onhfun + de == 
        glucosenhfun + 
          fructosenhfun, "EC 3.2.1.48 Sucrose alpha-glucosidase", "sucrose+h2o=glucose+fructose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      lactosenhfun + h2onhfun + de == 
        glucosenhfun + 
          galactosenhfun, "EC 3.2.1.108 Lactase", "lactose+h2oglucose+galactose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      inosinenhfun + h2onhfun + de == 
        hypoxanthinenhfun + 
          ribosenhfun, "EC 3.2.2.2 Inosine nucleosidase", "inosine+h2o=hypoxanthine+ribose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ampnhfun + h2onhfun + de == 
        adeninenhfun + 
          ribose5phosnhfun, "EC 3.2.2.4 AMP nucleosidase", "amp+h2o=adenine+ribose5phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adenosinenhfun + h2onhfun + de == 
        adeninenhfun + 
          ribosenhfun, "EC 3.2.2.7 Purinenucleosidase", "adenosine+h2o=adenine+ribose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      impnhfun + h2onhfun + de == 
        hypoxanthinenhfun + 
          ribose5phosnhfun, "EC 3.2.2.12 Inosinate nucleosidase", "imp+h2o=hypoxanthine+ribose5phos", {5, 6, 7, 8, 9}]\)

EC 3.5  Acting on carbon-nitrogen bonds, other than peptide bnds

\(chgNHbindSummary[
      asparagineLnhfun + h2onhfun + de == 
        aspartatenhfun + 
          ammonianhfun, "EC 3.5.1.1 Asparaginease", "asparagineL+h2o=aspartate+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glutaminenhfun + h2onhfun + de == 
        glutamatenhfun + 
          ammonianhfun, "EC 3.5.1.2 Glutaminase", "glutamine+h2o=glutamate+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ureanhfun + 2*h2onhfun + de == 
        co2totnhfun + 
          2*ammonianhfun, "EC 3.5.1.5 Urease", "urea+2*h2o=co2tot+2*ammonia", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[(creatinenhfun + de == 
            creatininenhfun + h2onhfun) // 
        N, "EC 3.5.2.10 Creatininase", "creatine=creatinine+h2o", {5, 
        6, 7, 8, 9}]

\(chgNHbindSummary[
      adeninenhfun + h2onhfun + de == 
        hypoxanthinenhfun + 
          ammonianhfun, "EC 3.5.4.2 Adenine deaminase", "adenine+h2o=hypoxanthine+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adenosinenhfun + h2onhfun + de == 
        inosinenhfun + 
          ammonianhfun, "EC 3.5.4.4 Adenosine deaminase", "adenosine+h2o=inosine+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ampnhfun + h2onhfun + de == 
        impnhfun + 
          ammonianhfun, "EC 3.5.4.6 AMP deaminase", "amp+h2o=imp+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      adpnhfun + h2onhfun + de == 
        idpnhfun + 
          ammonianhfun, "EC 3.5.4.7 ADP deaminase", "adp+h2o=idp+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + h2onhfun + de == 
        itpnhfun + 
          ammonianhfun, "EC 3.5.4.18 ATP deaminase", "atp+h2o=itp+ammonia", {5, 6, 7, 8, 9}]\)

EC 3.6  Acting on acid anhydrides

\(chgNHbindSummary[
      ppinhfun + h2onhfun + de == 
        2*pinhfun, "EC 3.6.1.1 Inorganic diphosphatase", "ppi+h2o=2*pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + h2onhfun + de == 
        adpnhfun + 
          pinhfun, "EC 3.6.1.3 Adenosinetriphosphatase", "atp+h2o=adp+pi", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      atpnhfun + 2*h2onhfun + de == 
        ampnhfun + 
          2*pinhfun, "EC 3.6.1.5 Apyrase", "atp+2*h2o=amp+2*pi", {5, 
        6, 7, 8, 9}]

\(chgNHbindSummary[
      atpnhfun + h2onhfun + de == 
        ampnhfun + 
          ppinhfun, "EC 3.6.1.8 ATP diphosphatase", "atp+h2o=amp+ppi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      fadoxnhfun + h2onhfun + de == 
        ampnhfun + 
          fmnoxnhfun, "EC 3.6.1.18 FAD diphophatase", "fadox+h2o=amp+fmnox", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      nadoxnhfun + h2onhfun + de == 
        ampnhfun + 
          nicotinamideribonucleotidenhfun, "EC 3.6.1.22 NADox diphosphatase\
", "nadox+h2o=amp+nicotinamideribonucleotide", {5, 6, 7, 8, 
        9}]

EC 3.7  Acting on carbon-carbon bonds

\(chgNHbindSummary[
      oxaloacetatenhfun + h2onhfun + de == 
        oxalatenhfun + 
          acetatenhfun, "EC 3.7.1.1 Oxaloacetase", "oxaloacetate=oxalate+acetate", {5, 6, 7, 8, 9}]\)

12.4  Lyase Reactions

EC 4.1  Carbon-carbon lyases

\(chgNHbindSummary[
      pyruvatenhfun + h2onhfun + de == 
        co2totnhfun + 
          acetaldehydenhfun, "EC 4.1.1.1 pyruvate decarboxylase", "pyruvate+h2o=co2tot+acetaldehyde", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      oxalatenhfun + h2onhfun + de == 
        co2totnhfun + 
          formatenhfun, "EC 4.1.1.2 Pyruvate decarboxylase", "oxalate+h2o=co2tot+formate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetoacetatenhfun + h2onhfun + de == 
        co2totnhfun + 
          acetonenhfun, "EC 4.1.1.4 Acetoacetate decarboxylase", "acetoacetate+h2o=co2tot+acetone", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      aspartatenhfun + h2onhfun + de == 
        co2totnhfun + 
          alaninenhfun, "EC 4.1.1.12 Aspartate 4-decarboxylase", "aspartate+h2o=co2tot+alanine", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      pyruvatenhfun + oxaloacetatenhfun + de == 
        co2totnhfun + 
          pepnhfun, "EC 4.1.1.31 Phosphoenolpyruvate carboxylase", "pyruvate+oxaloacetate=co2tot+pep", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      idpnhfun + co2totnhfun + pepnhfun + de == 
        itpnhfun + oxaloacetatenhfun + 
          h2onhfun, "EC 4.1.1.32 Phosphoenolpyruvate carboxykinase", "idp+co2tot+pep=itp+oxaloacetate+h2o", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      glyceraldehydephosnhfun + acetaldehydenhfun + de == 
        deoxyribose5phosnhfun, "EC 4.1.2.4 Deoxyribose-phosphate \
aldolase", "glyceraldehydephos+acetaldehyde=deoxyribose5phos", {5, 6, 
        7, 8, 9}]

\(chgNHbindSummary[
      dihydroxyacetonephosnhfun + glyceraldehydephosnhfun + de == 
        fructose16phosnhfun, "EC 4.1.2.13a Fructose-bisphosphate aldolase", "dihydroxyacetonephos+glyceraldehydephos+de==fructose16phos", {5, 6, 7, 
        8, 9}]\)

chgNHbindSummary[
      2*dihydroxyacetonephosnhfun + de == 
        fructose16phosnhfun, "EC 4.1.2.13b Fructose-bisphosphate \
aldolase", "2*dihydroxyacetonephos=fructose16phos", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[\((formatenhfun + acetaldehydenhfun + de == 
            lactatenhfun)\) // 
        N, "EC 4.1.2.36 Lactate aldolase", "formate+acetaldehyde=lactate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      succinatenhfun + glyoxylatenhfun + de == 
        citrateisonhfun, "EC 4.1.3.1 Isocitratelyase", "succinate+glyoxylate=citrateiso", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetatenhfun + oxaloacetatenhfun + de == 
        citratenhfun, "EC 4.1.3.6 Citrate(pro-3S)-lyase", "acetate+oxaloacetate=citrate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[\((pyruvatenhfun + glyoxylatenhfun + de == 
            hydroxy2oxoglutaratenhfun)\) // 
        N, "EC 4.1.3.16 4-hydroxy-2-oxoglutarate aldolase", "pyruvate+glyoxylate=hydroxy2oxoglutarate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      tryptophanLnhfun + h2onhfun + de == 
        indolenhfun + 
          pyruvatenhfun, "EC 4.1.99.1 Tryptophanasease", "tryptophanL+h2o=indole+pyruvate", {5, 6, 7, 8, 9}]\)

EC 4.2  Carbon-oxygen lyases

\(chgNHbindSummary[
      fumaratenhfun + h2onhfun + de == 
        malatenhfun, "EC 4.2.1.2 Fumarate hydratase", "fumarate+h2o=malate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      aconitatecisnhfun + h2onhfun + de == 
        citratenhfun, "EC 4.2.1.3 Aconitate hydratase", "aconitatecis+h2o=citrate", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      phosphoglycerate2nhfun + de == 
        pepnhfun + 
          h2onhfun, "EC 4.2.1.11 Phosphoenolpyruvate hydratase", "phosphoglycerate2=pep+h2o", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      maleatenhfun + h2onhfun + de == 
        malatenhfun, "EC 4.2.1.31 Maleate hydratase", "maleate+h2o=malate", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      methylmaleatenhfun + h2onhfun + de == 
        methylmalatenhfun, "EC 4.2.1.35 (R)-2methylmalate dehydratase", "\
methylmaleate+h2o=methylmalate", {5, 6, 7, 8, 9}]

EC 4.3  Carbon-nitrogen lyases

\(chgNHbindSummary[
      fumaratenhfun + ammonianhfun + de == 
        aspartatenhfun, "EC 4.3.1.1 Aspartate ammonia-lyase", "aspartate+de==fumarate+ammonia", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      serineLnhfun + de == 
        pyruvatenhfun + 
          ammonianhfun, "EC 4.3.1.17 L-serine ammonia-lyase", "serineL=pyruvate+ammonia", {5, 6, 7, 8, 9}]\)

EC 4.4  Carbon-sulfur lyases

\(chgNHbindSummary[
      cysteineLnhfun + h2onhfun + de == 
        h2saqnhfun + ammonianhfun + 
          pyruvatenhfun, "EC 4.4.1.15 D-cysteine desulfhydratase", "cysteineL+h2o=h2saq+ammonia+pyruvate", {5, 6, 7, 8, 9}]\)

EC 4.6  Phosphorus-oxygen lyases

\(chgNHbindSummary[
      cyclicampnhfun + ppinhfun + de == 
        atpnhfun, "EC 4.6.1.1 Adenylate cyclase", "atp=cyclicamp+ppi", {5, 6, 7, 8, 9}]\)

12.5  Isomerase Reactions

EC 5.2  Cis-trans-isomerases

\(chgNHbindSummary[
      maleatenhfun + de == 
        fumaratenhfun, "EC 5.2.1.1 Maleate isomerase", "maleate=fumarate", {5, 6, 7, 8, 9}]\)

EC 5.3  Intramolecular oxidoreductases

chgNHbindSummary[
      glyceraldehydephosnhfun + de == 
        dihydroxyacetonephosnhfun, "EC 5.3.1.1 Triosephosphate \
isomerase", "glyceraldehydephos=dihydroxyacetonephos", {5, 6, 7, 8, 
        9}]

\(chgNHbindSummary[
      xylulosenhfun + de == 
        xylosenhfun, "EC 5.3.1.5 Xylose isomerase", "xylulose=xylose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ribose1phosnhfun + de == 
        ribose5phosnhfun, "EC 5.3.1.6 Ribose-5-phosphate isomerase", "ribose1phos=ribose5phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      mannosenhfun + de == 
        fructosenhfun, "EC 5.3.1.7 mannose isomerase", "mannose=fructose", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      mannose6phosnhfun + de == 
        fructose6phosnhfun, "EC 5.3.1.8 Mannose-6-phosphate isomerase", "\
mannose6phos=fructose6phos", {5, 6, 7, 8, 9}]

\(chgNHbindSummary[
      fructose6phosnhfun + de == 
        glucose6phosnhfun, "EC 5.3.1.9 Glucose-6-phosphate isomerase", "fructose6phos=glucose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      xylulosenhfun + de == 
        lyxosenhfun, "EC 5.3.1.15 D-lyxose keto-isomerase", "xylulose=lyxose", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      ribulosenhfun + de == 
        ribosenhfun, "EC 5.3.1.20 Ribose isomerase", "ribulose=ribose", {5, 6, 7, 8, 9}]\)

EC 5.4  Intramolecular transferases (mutases)

\(chgNHbindSummary[
      glucose1phosnhfun + de == 
        glucose6phosnhfun, "EC 5.4.2.6 Beta-phosphoglucomutase", "glucose1phos=glucose6phos", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      mannose1phosnhfun + de == 
        mannose6phosnhfun, "EC 5.4.2.8 Phosphomannomutase", "mannose1phos=mannose6phos", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      maltosenhfun + de == 
        trehalosenhfun, "EC 5.4.99.16 Maltose \
alpha-D-glucosyltransferase", "maltose=trehalose", {5, 6, 7, 8, 
        9}]

12.6  Ligase Reactions

EC 6.2  Forming carbon-sulfur bonds

\(chgNHbindSummary[
      acetatenhfun + atpnhfun + coAnhfun + de == 
        acetylcoAnhfun + ampnhfun + 
          ppinhfun, "EC 6.2.1.1 Acetate-CoA ligase", "acetate+atp+coA=acetylcoA+amp+ppi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      succinatenhfun + atpnhfun + coAnhfun + de == 
        succinylcoAnhfun + adpnhfun + 
          pinhfun, "EC 6.2.1.5 Succinate-CoA ligase (ADP forming)", "succinate+atp+coA=succinylcoA+adp+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      oxalatenhfun + atpnhfun + coAnhfun + de == 
        oxalylcoAnhfun + adpnhfun + 
          pinhfun, "EC 6.2.1.8 Oxalate-CoA ligase", "oxalate+atp+coA=oxalylcoA+adp+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      malatenhfun + atpnhfun + coAnhfun + de == 
        malylcoAnhfun + adpnhfun + 
          pinhfun, "EC 6.2.1.9 Oxalate-CoA ligase", "malate+atp+coA=malylcoA+adp+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetylcoAnhfun + adpnhfun + pinhfun + de == 
        acetatenhfun + atpnhfun + 
          coAnhfun, "EC 6.2.1.13 acetate-CoA ligase (ADP forming)", "acetylcoA+adp+pi=acetate+atp+coA", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      acetoacetylcoAnhfun + ampnhfun + ppinhfun + de == 
        acetoacetatenhfun + atpnhfun + 
          coAnhfun, "EC 6.2.1.16 Acetoacetate-CoA ligase", "acetoacetylcoA+amp+ppi=acetoacetate+atp+coA", {5, 6, 7, 8, 
        9}]\)

EC 6.3  Forming carbon-nitrogen bonds

\(chgNHbindSummary[
      aspartatenhfun + atpnhfun + ammonianhfun + de == 
        asparagineLnhfun + ampnhfun + 
          ppinhfun, "EC 6.3.1.1 Aspartate-ammonia ligase", "aspartate+atp+ammonia=asparagineL+amp+ppi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      glutamatenhfun + atpnhfun + ammonianhfun + de == 
        asparagineLnhfun + adpnhfun + 
          pinhfun, "EC 6.3.1.2 Glutamate-ammonia ligase", "glutamate+atp+ammonia=asparagineL+adp+pi", {5, 6, 7, 8, 9}]\)

chgNHbindSummary[
      aspartatenhfun + atpnhfun + ammonianhfun + de == 
        asparagineLnhfun + adpnhfun + 
          pinhfun, "EC 6.3.1.4 Aspartate-ammonia ligase (ADP-forming)", "\
aspartate+atp+ammonia=asparagineL+adp+pi", {5, 6, 7, 8, 9}]

chgNHbindSummary[
      aspartatenhfun + atpnhfun + glutaminenhfun + de == 
        asparagineLnhfun + glutamatenhfun + ampnhfun + 
          ppinhfun, "EC 6.3.5.4 Asparagine synthase (glutamine-hydrolyzing)\
", "aspartate+atp+glutamine=asparagineL+glutamate+amp+ppi", {5, 6, 7, 
        8, 9}]

EC 6.4  Forming carbon-carbon bonds

\(chgNHbindSummary[
      atpnhfun + pyruvatenhfun + co2totnhfun + de == 
        oxaloacetatenhfun + adpnhfun + 
          pinhfun, "EC 6.4.1.1 Pyruvate carboxylase", "atp+pyruvate+co2tot=oxaloacetate+adp+pi", {5, 6, 7, 8, 9}]\)

\(chgNHbindSummary[
      atpnhfun + propanoylcoAnhfun + co2totnhfun + de == 
        methylmalonylcoAnhfun + adpnhfun + 
          pinhfun, "EC 6.4.1.3 Propanoyl-CoA carboxylase", "atp+propanoylcoA+co2tot=methylmalonylcoA+adp+pi", {5, 6, 7, 8, 
        9}]\)

\(chgNHbindSummary[
      acetonenhfun + co2totnhfun + atpnhfun + h2onhfun + de == 
        acetoacetatenhfun + ampnhfun + 
          2*pinhfun, "EC 6.4.1.6 Acetone carboxylase", "acetone+co2tot+atp+h2o=acetoacetate+amp+2*pi", {5, 6, 7, 8, 
        9}]\)

6. Discussion

These calculations of changes in the binding of hydrogen ions in enzyme-catalyzed reactions at 298.15 K and 025 M ionic strength using the pKs of the reactants confirm the previous calculations of (Subscript[Δ, r]) (Subscript[N, H])  using the partial derivative of the standard transformed Gibbs energy of reaction with respect to pH (1).  This shows that (Subscript[Δ, r]) (Subscript[N, H]) can be calculated for enzyme-catalyzed reactions for which (Subscript[Δ, r]) G' ° are not available, provided that pKs for the reactants in these reactions are known or can be estimated from knowledge of pKs of reactants with similar structures.  The pKs at 298.15 K for 60 weak acids of biochemical interest (4) can be used to make these estimates.

7. References

1. R. A. Alberty, Biochemical Thermodynamics: Applications of Mathematica, Wiley, Hoboken, NJ (2006).

2.   R .  A .  Alberty,BasicBiochemData3 . nb (2005).
http: // library . wolfram . com/
                      infocenter/MathSource/5704

3.  R. A. Alberty and R. N. Goldberg, Calculation of thermodynamic formation properties for the ATP series at specified pH and pMg. Biochem. 31, 10610-10615 (1992).

4. R. A. Alberty, Thermodynamic properties of weak acids involved in enzyme-catalyzed reactions, J. Phys. Chem. B , 110, 5012-5016 (2006).