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MetaCyc Compound: NADPH

Synonyms: reduced nicotinamide adenine dinucleotide phosphate, NADPH2, NADPH2, dihydrotriphosphopyridine nucleotide, reduced dihydrotriphosphopyridine nucleotide, dihydronicotinamide adenine dinucleotide phosphate, dihydronicotinamide adenine dinucleotide phosphate reduced, reduced NADP, NADP-red, TPNH, dihydronicotinamide adenine dinucleotide-P, β-NADPH

Superclasses: a nucleic acid component a nucleotide a dinucleotide a dinucleotide electron carrier NAD(P)H
a nucleic acid component a nucleotide a dinucleotide electron carrier NAD(P)H
a nucleic acid component an oligonucleotide a dinucleotide a dinucleotide electron carrier NAD(P)H
an acceptor a redox electron carrier NAD(P)H

Summary:
NAD+ and NADP+ are dinucleotides containing one nicotinamide base and one adenine base. Each nucleotide is connected to a ribose sugar at position 1, and the two riboses are connected at their 5 position via a diphosphate. The only difference between the two is that in NADP there is an additional phosphate group at the 2' position of the ribose that carries the adenine moiety.

These molecules are biological carriers of reductive equivalents (i.e. high potential electrons). They are often referred to as coenzymes, although in most of their reactions they function as cosubstrates rather than true coenzymes.

The most common function of NAD+ is to accept two electrons and a proton (a hydride ion) from a substrate that is being oxidized. This reduction converts NAD+ to NADH, the reduced form. NADH then diffuses or is being transported to a terminal oxidase, where the electrons are passed on, regenerating the oxidized form.

NADPH, on the other hand, is mostly involved in biosynthetic reactions, where it serves as an electron donor. NADPH is formed by reduction of NADP+, which occurs by different mechanisms in different types of organisms. In photosynthetic organisms NADP+ is reduced by photosystem I. In heterotrophic organisms it is reduced by central metabolism processes such as the pentose phosphate pathway (see pentose phosphate pathway (oxidative branch)).

Chemical Formula: C21H26N7O17P3

Molecular Weight: 741.39 Daltons

Monoisotopic Molecular Weight: 745.0911021051 Daltons

NADPH compound structure

SMILES: C5(N(C1(OC(C(C1O)O)COP(OP(OCC4(C(C(C(N3(C2(=C(C(=NC=N2)N)N=C3)))O4)OP([O-])([O-])=O)O))([O-])=O)(=O)[O-]))C=C(CC=5)C(=O)N)

InChI: InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/p-4/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChIKey: InChIKey=ACFIXJIJDZMPPO-NNYOXOHSSA-J

Unification Links: CAS:2646-71-1 , ChEBI:57783 , ChemSpider:10239199 , HMDB:HMDB00221 , IAF1260:33486 , KEGG:C00005 , MetaboLights:MTBLC57783 , PubChem:15983949

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -551.72284 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(+)-camphor degradation , (-)-camphor degradation :
[(1R)-2,2,3-trimethyl-5-oxocyclopent-3-enyl]acetyl-CoA + NADPH + H+ + oxygen → [(2R)-3,3,4-trimethyl-6-oxo-3,6-dihydro-1H-pyran-2-yl]acetyl-CoA + NADP+ + H2O

(1'S,5'S)-averufin biosynthesis :
(1'S)-averantin + NADPH + H+ + oxygen → (1'S,5'R)-hydroxyaverantin + NADP+ + H2O
(1'S)-averantin + NADPH + H+ + oxygen → (1'S,5'S)-hydroxyaverantin + NADP+ + H2O

(3E)-4,8-dimethylnona-1,3,7-triene biosynthesis :
(3S,6E)-nerolidol + NADPH + H+ + oxygen → (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O
(3R,6E)-nerolidol + NADPH + H+ + oxygen → (3E)-4,8-dimethylnona-1,3,7-triene + but-1-en-3-one + NADP+ + 2 H2O

(4R)-carveol and (4R)-dihydrocarveol degradation :
(+)-isodihydrocarvone + NADPH + oxygen + H+ → (3S,6R)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
(+)-dihydrocarvone + NADPH + H+ + oxygen → (4R,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

(4R)-carvone biosynthesis :
(4S)-limonene + NADPH + oxygen + H+ → (-)-trans-carveol + NADP+ + H2O

(4S)-carveol and (4S)-dihydrocarveol degradation :
(-)-dihydrocarvone + NADPH + oxygen + H+ → (3S,6S)-6-isopropenyl-3-methyloxepan-2-one + NADP+ + H2O
(-)-isodihydrocarvone + NADPH + H+ + oxygen → (4S,7R)-4-isopropenyl-7-methyloxepan-2-one + NADP+ + H2O

(4S)-carvone biosynthesis :
(4R)-limonene + NADPH + H+ + oxygen → (+)-trans-carveol + NADP+ + H2O

(5Z)-dodec-5-enoate biosynthesis :
a (3R,5Z)-3-hydroxy-dodec-5-enoyl-[acp] + NADP+ ← a (5Z)-3-oxo-dodec-5-enoyl-[acp] + NADPH + H+

(E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraene biosynthesis :
(E,E)-geranyllinalool + NADPH + H+ + oxygen → 4,8,12-trimethyl-1,3,7,11-tridecatetraene + but-1-en-3-one + NADP+ + 2 H2O

(R)- and (S)-3-hydroxybutanoate biosynthesis , acetyl-CoA fermentation to butanoate II , ethylmalonyl-CoA pathway , polyhydroxybutanoate biosynthesis :
(R)-3-hydroxybutanoyl-CoA + NADP+ ← acetoacetyl-CoA + NADPH + H+

(R)-canadine biosynthesis :
7,8-dihydroberberine + NADPH + H+ → (R)-canadine + NADP+
berberine + NADPH → 7,8-dihydroberberine + NADP+

(S)-reticuline biosynthesis I :
(S)-N-methylcoclaurine + NADPH + oxygen + H+ → 3'-hydroxy-N-methyl-(S)-coclaurine + NADP+ + H2O

(Z)-9-tricosene biosynthesis :
(15Z)-tetracos-15-enal + NADPH + oxygen + H+ → (Z)-9-tricosene + CO2 + NADP+ + H2O

1,2-propanediol biosynthesis from lactate (engineered) :
(R)-propane-1,2-diol + NADP+ ← (R)-lactaldehyde + NADPH + H+
(S)-propane-1,2-diol + NADP+ ← (S)-lactaldehyde + NADPH + H+

1,3-propanediol biosynthesis (engineered) :
1,3-propanediol + NADP+ ← 3-hydroxypropionaldehyde + NADPH + H+

1,8-cineole degradation :
6-oxocineole + NADPH + oxygen + H+ → 1,6,6-trimethyl-2,7-dioxobicyclo-(3,2,2)nonan-3-one + NADP+ + H2O

10-cis-heptadecenoyl-CoA degradation (yeast) :
2-trans, 4-cis-undecadienoyl-CoA + NADPH + H+ → 3-trans-undecenoyl-CoA + NADP+

10-trans-heptadecenoyl-CoA degradation (reductase-dependent, yeast) :
2-trans, 4-trans-undecadienoyl-CoA + NADPH + H+ → 3-trans-undecenoyl-CoA + NADP+

11-cis-3-hydroxyretinal biosynthesis :
a (3R)-all-trans-3-hydroxyretinol-[retinoid-binding protein] + NADP+ ← a (3R)-all-trans-3-hydroxyretinal-[retinoid-binding protein] + NADPH + H+

Reactions known to produce the compound:

(4R)-carvone biosynthesis :
(-)-trans-carveol + NADP+R-(-)-carvone + NADPH + H+

11-cis-3-hydroxyretinal biosynthesis :
a (3S)-11-cis-3-hydroxyretinol-[retinoid-binding protein] + NADP+ → a (3S)-11-cis-3-hydroxyretinal-[retinoid-binding protein] + NADPH + H+

2,3-dihydroxypropane-1-sulfonate degradation :
(S)-2,3-dihydroxypropane 1-sulfonate + NADP+ → 2-oxo-3-hydroxy-propane-1-sulfonate + NADPH + H+

3,6-anhydro-α-L-galactopyranose degradation :
3,6-anhydro-α-L-galactofuranose + NADP+ + H2O → 3,6-anhydro-α-L-galactonate + NADPH + 2 H+

3-amino-4,7-dihydroxy-coumarin biosynthesis :
(R)-β-hydroxy-L-tyrosine-S-[NovH protein] + NADP+ → β-oxo-L-tyrosine-S-[NovH protein] + NADPH + H+

4-aminobutanoate degradation II , 4-hydroxyphenylacetate degradation , nicotine degradation I (pyridine pathway) , TCA cycle IV (2-oxoglutarate decarboxylase) :
succinate semialdehyde + NADP+ + H2O → succinate + NADPH + 2 H+

4-hydroxymandelate degradation :
4-hydroxybenzaldehyde + NADP+ + H2O → 4-hydroxybenzoate + NADPH + 2 H+

7-dehydroporiferasterol biosynthesis :
porifersta-5,7-dienol + NADP+ → 7-dehydroporiferasterol + NADPH + H+

apicidin biosynthesis :
L-2-amino-8-hydroxydecanoate + NADP+L-2-amino-8-oxodecanoate + NADPH + H+

benzoate biosynthesis I (CoA-dependent, β-oxidative) , benzoyl-CoA biosynthesis :
3-hydroxy-3-phenylpropanoyl-CoA + NADP+ → 3-oxo-3-phenylpropanoyl-CoA + NADPH + H+

benzoyl-CoA degradation I (aerobic) :
cis-3,4-dehydroadipyl-CoA semialdehyde + NADP+ + H2O → cis-3,4-dehydroadipyl-CoA + NADPH + 2 H+

brassinosteroid biosynthesis I :
6-hydroxytyphasterol + NADP+ → typhasterol + NADPH + H+
6-hydroxyteasterone + NADP+ → teasterone + NADPH + H+
3-dehydro-6-hydroxyteasterone + NADP+ → 3-dehydroteasterone + NADPH + H+
6α-hydroxy-castasterone + NADP+ → castasterone + NADPH + H+

C4 photosynthetic carbon assimilation cycle, NADP-ME type , C4 photosynthetic carbon assimilation cycle, PEPCK type , gluconeogenesis I :
(S)-malate + NADP+ → CO2 + pyruvate + NADPH

camalexin biosynthesis :
indole-3-acetonitrile-cysteine conjugate + NADP+ → dihydrocamalexate + hydrogen cyanide + NADPH + 2 H+

chlorophyllide a biosynthesis II (anaerobic) :
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ → 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+
131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ → 2,4-divinyl protochlorophyllide a + NADPH + 2 H+
magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O → 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+

costunolide biosynthesis :
germacra-1(10),4,11(13)-trien-12-al + NADP+ + H2O → germacra-1(10),4,11(13)-trien-12-oate + NADPH + 2 H+
germacra-1(10),4,11(13)-trien-12-ol + NADP+ → germacra-1(10),4,11(13)-trien-12-al + NADPH + H+

cutin biosynthesis :
18-hydroxyoleate + NADP+ → 18-oxo-oleate + NADPH + H+
18-oxo-oleate + NADP+ + H2O → α,ω-9Z-octadecenedioate + NADPH + 2 H+
16-hydroxypalmitate + NADP+ → 16-oxo-palmitate + NADPH + H+

Reactions known to both consume and produce the compound:

(1'S,5'S)-averufin biosynthesis :
(1'S)-averantin + NADP+ ↔ norsolorinate + NADPH + H+

3-hydroxypropanoate cycle , 3-hydroxypropanoate/4-hydroxybutanate cycle , glyoxylate assimilation :
3-oxopropanoate + coenzyme A + NADP+ ↔ malonyl-CoA + NADPH + H+

4-amino-2-methyl-5-phosphomethylpyrimidine biosynthesis (yeast) , pyridoxal 5'-phosphate salvage II (plants) :
pyridoxine + NADP+ ↔ pyridoxal + NADPH + H+

acetone degradation I (to methylglyoxal) :
isopropanol + NADP+ ↔ acetone + NADPH + H+
acetol + NADP+ ↔ methylglyoxal + NADPH + H+

acetone degradation II (to acetoacetate) , acetone degradation III (to propane-1,2-diol) , isopropanol biosynthesis :
isopropanol + NADP+ ↔ acetone + NADPH + H+

acetyl-CoA biosynthesis II (NADP-dependent pyruvate dehydrogenase) :
pyruvate + coenzyme A + NADP+ ↔ acetyl-CoA + CO2 + NADPH

ajmaline and sarpagine biosynthesis :
geissoschizine + NADP+ ↔ 4,21-dehydrogeissoschizine + NADPH

carbon tetrachloride degradation II :
formate + NADP+ ↔ CO2 + NADPH

chorismate biosynthesis from 3-dehydroquinate :
shikimate + NADP+ ↔ 3-dehydroshikimate + NADPH + H+

cinchona alkaloids biosynthesis :
cinchonidine + cinchonine + 2 NADP+ ↔ 2 cinchoninone + 2 NADPH + 4 H+
quinine + quinidine + 2 NADP+ ↔ 2 quinidinone + 2 NADPH + 4 H+

clavulanate biosynthesis :
clavaldehyde + NADPH + H+ ↔ clavulanate + NADP+

cob(II)yrinate a,c-diamide biosynthesis II (late cobalt incorporation) :
precorrin-6B + NADP+ ↔ precorrin-6A + NADPH + H+

cocaine biosynthesis :
ecgonine methyl ester + NADP+ ↔ methyl ecgonone + NADPH + 2 H+

D-galacturonate degradation III , L-ascorbate biosynthesis V :
aldehydo-L-galactonate + NADP+aldehydo-D-galacturonate + NADPH + H+

D-glucuronate degradation I :
xylitol + NADP+ ↔ L-xylulose + NADPH + H+

detoxification of reactive carbonyls in chloroplasts , methylglyoxal degradation III :
acetol + NADP+ ↔ methylglyoxal + NADPH + H+

ectoine biosynthesis , grixazone biosynthesis , L-homoserine biosynthesis , L-lysine biosynthesis I , L-lysine biosynthesis II , L-lysine biosynthesis VI , norspermidine biosynthesis , spermidine biosynthesis II :
L-aspartate-semialdehyde + NADP+ + phosphate ↔ L-aspartyl-4-phosphate + NADPH + H+

ethylene biosynthesis V (engineered) , L-glutamine biosynthesis III , methylaspartate cycle , mixed acid fermentation , NAD/NADP-NADH/NADPH cytosolic interconversion (yeast) , reductive TCA cycle I , TCA cycle I (prokaryotic) , TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) , TCA cycle VII (acetate-producers) , TCA cycle VIII (helicobacter) :
D-threo-isocitrate + NADP+ ↔ 2-oxoglutarate + CO2 + NADPH

ethylmalonyl-CoA pathway :
(2S)-ethylmalonyl-CoA + NADP+ ↔ crotonyl-CoA + CO2 + NADPH

farnesylcysteine salvage pathway , juvenile hormone III biosynthesis I , juvenile hormone III biosynthesis II :
(2E,6E)-farnesol + NADP+ ↔ (2E,6E)-farnesal + NADPH + H+

folate transformations I , folate transformations II , formate reduction to 5,10-methylenetetrahydrofolate , N10-formyl-tetrahydrofolate biosynthesis , purine nucleobases degradation II (anaerobic) :
a 5,10-methylene-tetrahydrofolate + NADP+ ↔ a 5,10-methenyltetrahydrofolate + NADPH

galactose degradation IV :
galactitol + NADP+ ↔ β-D-galactose + NADPH + H+
L-xylo-3-hexulose + NADPH + H+ ↔ D-sorbitol + NADP+

In Reactions of unknown directionality:

(8E,10E)-dodeca-8,10-dienol biosynthesis :
(8E,10E)-dodeca-8,10-dienoate + 2 NADPH + 3 H+ = (8E,10E)-dodeca-8,10-dienol + 2 NADP+ + H2O

CDP-abequose biosynthesis :
CDP-α-D-abequose + NADP+ = CDP-4-dehydro-3,6-dideoxy-D-glucose + NADPH + H+

chrysophanol biosynthesis :
emodin + NADPH + 2 H+ = chrysophanol + NADP+ + H2O

fatty acids biosynthesis (yeast) :
acetyl-CoA + n malonyl-CoA + 2n NADPH + 4n H+ = a long-chain acyl-CoA + n CO2 + n coenzyme A + 2n NADP+

Not in pathways:
(S)-propane-1,2-diol + NADP+ = (S)-lactaldehyde + NADPH + H+
chlordecone alcohol + NADP+ = chlordecone + NADPH + H+
(2S)-flavan-4-ol + NADP+ = (2S)-flavanone + NADPH + H+
prostaglandin F + NADP+ = prostaglandin D2 + NADPH + H+
diethyl (2R,3R)-2-methyl-3-hydroxysuccinate + NADP+ = diethyl-2-methyl-3-oxosuccinate + NADPH + H+
5-α-androstan-3β,17β-diol + NADP+ = 5-α-dihydrotestosterone + NADPH + H+
coformycin + NADP+ = 8-oxocoformycin + NADPH + 2 H+
glycerol + NADP+ = dihydroxyacetone + NADPH + H+
dihydrozeatin + NADP+ = trans-zeatin + NADPH + H+
N5-(L-1-carboxyethyl)-L-ornithine + NADP+ + H2O = pyruvate + L-ornithine + NADPH + H+
3-methyloxindole + NADP+ = 3-methyleneoxindole + NADPH + H+
ethyl (S)-3-hydroxyhexanoate + NADP+ = ethyl-3-oxohexanoate + NADPH + H+
ethyl (R)-3-hydroxyhexanoate + NADP+ = ethyl-3-oxohexanoate + NADPH + H+
scytalone + NADP+ = 1,3,6,8-naphthalenetetrol + NADPH + H+
glutathione + coenzyme A + NADP+ = CoA-glutathione + NADPH + H+
prostaglandin I2 + NADP+ = 15-dehydro-prostaglandin I2 + NADPH + H+
prostaglandin F + NADP+ = prostaglandin E2 + NADPH + H+
benzyl (2r,3s)-2-methyl-3-hydroxybutanoate + NADP+ = benzyl-2-methyl-3-oxobutanoate + NADPH + H+
3-β-hydroxy-5-β-pregnane-20-one + NADP+ = 5-β-pregnan-3,20 dione + NADPH + H+
a trans-2-enoyl-CoA + NADP+ = a trans-2,trans-4-dienoyl-CoA + NADPH + H+
(+-)-5-[(tert-butylamino)-2'-hydroxypropoxy]-1,2,3,4-tetrahydro-1-naphthol + NADP+ = (+-)-5-[(tert-butylamino)-2'-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone + NADPH + H+

In Redox half-reactions:
NADP+[in] + H+[in] + 2 e-[membrane]NADPH[in] ,
NAD(P)+[in] + H+[in] + 2 e-[membrane]NAD(P)H[in]

Enzymes activated by NADPH, sorted by the type of activation, are:

Activator (Mechanism unknown) of: prolycopene isomerase [Isaacson04]

Enzymes inhibited by NADPH, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: isocitrate dehydrogenase kinase [Nimmo84, Miller00a] , isocitrate dehydrogenase phosphatase [Nimmo84, Miller00a] , biotin sulfoxide reductase [Comment 1] , NAD+-dependent glyceraldehyde-3-phosphate dehydrogenase [Brunner98] , arogenate dehydrogenase [Rippert02] , L-xylulose reductase [Witteveen94]

Inhibitor (Noncompetitive) of: phosphate acetyltransferase [Suzuki69, Comment 2]

Inhibitor (Allosteric) of: NAD kinase [Kawai01, Zerez87]

Inhibitor (Mechanism unknown) of: glutathione reductase [Mata84, Comment 3] , glutaminase B [Prusiner76] , NADH kinase [Kawai01a] , NAD(+) kinase [Kawai01a] , aldehyde decarbonylase [SchneiderBelhad00] , D-galacturonate dehydrogenase [Wagner76] , imidazol-pyruvate reductase [Comment 4] , phosphotransbutyrylase [Comment 5] , UDP-D-glucose/UDP-D-galactose 4-epimerase [Barber06a] , GDP-D-mannose-3'',5''-epimerase [Wolucka03] , GDP-D-mannose:GDP-L-gulose epimerase [Wolucka03] , ethylnitronate monooxygenase [Kido78]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: 1-deoxy-D-xylulose 5-phosphate reductoisomerase , isopentenyl-diphosphate:NAD(P)+ oxidoreductase , dimethylallyl-diphosphate:NAD(P)+ oxidoreductase , HMP-P synthase , pyrroline-5-carboxylate reductase , glutamate-5-semialdehyde dehydrogenase , dechloro-dehydrogriseofulvin reductase , dehydrogriseofulvin reductase , prolycopene isomerase , aminopyrrolnitrin oxygenase , nicotine monooxygenase , bupropion hydroxylase , flavin-dependent thymidylate synthase , flavin-dependent thymidylate synthase , squalene,NADPH:oxygen oxidoreductase (2,3-epoxidizing) , germacrene A hydroxylase , squalene,hydrogen-donor:oxygen oxidoreductase (2,3-epoxidizing) , isocitrate dehydrogenase , fluorene 1,2-dioxygenase , mycothione reductase , 6-oxocineole oxygenase , fluorene monooxygenase , GDP-mannose 4,6-dehydratase

This compound has been characterized as an alternative cofactor or prosthetic group of the following enzymes: glycerol dehydrogenase

This compound has been characterized as an alternative substrate of the following enzymes: altronate oxidoreductase , D-octopine synthase , orcinol hydroxylase , 15-cis phytoene desaturase , NADH oxidoreductase , 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase , resorcinol hydroxylase , D-mannonate oxidoreductase , FAD-dependent urate hydroxylase , 5,10-methylenetetrahydrofolate reductase


References

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Brunner98: Brunner NA, Brinkmann H, Siebers B, Hensel R (1998). "NAD+-dependent glyceraldehyde-3-phosphate dehydrogenase from Thermoproteus tenax. The first identified archaeal member of the aldehyde dehydrogenase superfamily is a glycolytic enzyme with unusual regulatory properties." J Biol Chem 273(11);6149-56. PMID: 9497334

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Kawai01a: Kawai S, Suzuki S, Mori S, Murata K (2001). "Molecular cloning and identification of UTR1 of a yeast Saccharomyces cerevisiae as a gene encoding an NAD kinase." FEMS Microbiol Lett 200(2);181-4. PMID: 11425472

Kido78: Kido T, Soda K (1978). "Properties of 2-nitropropane dioxygenase of Hansenula mrakii. Formation and participation of superoxide." J Biol Chem 253(1);226-32. PMID: 201619

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mata84: Mata AM, Pinto MC, Lopez-Barea J (1984). "Purification by affinity chromatography of glutathione reductase (EC 1.6.4.2) from Escherichia coli and characterization of such enzyme." Z Naturforsch [C] 39(9-10);908-15. PMID: 6393625

Miller00a: Miller SP, Chen R, Karschnia EJ, Romfo C, Dean A, LaPorte DC (2000). "Locations of the regulatory sites for isocitrate dehydrogenase kinase/phosphatase." J Biol Chem 275(2);833-9. PMID: 10625615

Nimmo84: Nimmo GA, Nimmo HG (1984). "The regulatory properties of isocitrate dehydrogenase kinase and isocitrate dehydrogenase phosphatase from Escherichia coli ML308 and the roles of these activities in the control of isocitrate dehydrogenase." Eur J Biochem 1984;141(2);409-14. PMID: 6329757

Pollock01: Pollock, VV, Barber, MJ "Kinetic and mechanistic properties of biotin sulfoxide reductase." Biochemistry 40:1430-1440 (2001).

Prusiner76: Prusiner S, Stadtman ER (1976). "Regulation of glutaminase B in Escherichia coli. III. Control by nucleotides and divalent cations." J Biol Chem 1976;251(11);3463-9. PMID: 776970

Rippert02: Rippert P, Matringe M (2002). "Purification and kinetic analysis of the two recombinant arogenate dehydrogenase isoforms of Arabidopsis thaliana." Eur J Biochem 269(19);4753-61. PMID: 12354106

SchneiderBelhad00: Schneider-Belhaddad F, Kolattukudy P (2000). "Solubilization, partial purification, and characterization of a fatty aldehyde decarbonylase from a higher plant, Pisum sativum." Arch Biochem Biophys 377(2);341-9. PMID: 10845712

Suzuki69: Suzuki T (1969). "Phosphotransacetylase of Escherichia coli B, activation by pyruvate and inhibition by NADH and certain nucleotides." Biochim Biophys Acta 1969;191(3);559-69. PMID: 4312205

Wagner76: Wagner G, Hollmann S (1976). "Uronic acid dehydrogenase from Pseudomonas syringae. Purification and properties." Eur J Biochem 61(2);589-96. PMID: 2471

Wiesenborn89: Wiesenborn DP, Rudolph FB, Papoutsakis ET (1989). "Phosphotransbutyrylase from Clostridium acetobutylicum ATCC 824 and its role in acidogenesis." Appl Environ Microbiol 1989;55(2);317-22. PMID: 2719475

Witteveen94: Witteveen C. F. B., Weber F., Busink R., Visser J. (1994). "Isolation and characterization of two xylitol dehydrogenases from Aspergillus niger." Microbiology 140, 1679-1685.

Wolucka03: Wolucka BA, Van Montagu M (2003). "GDP-mannose 3',5'-epimerase forms GDP-L-gulose, a putative intermediate for the de novo biosynthesis of vitamin C in plants." J Biol Chem 278(48);47483-90. PMID: 12954627

Zerez87: Zerez CR, Moul DE, Gomez EG, Lopez VM, Andreoli AJ (1987). "Negative modulation of Escherichia coli NAD kinase by NADPH and NADH." J Bacteriol 1987;169(1);184-8. PMID: 3025169


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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