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Escherichia coli K-12 substr. MG1655 Compound: diphosphate

Synonyms: PPi, PP, pyrophosphate

Superclasses: an ion an anion an inorganic phosphorus-containing ion an inorganic phosphate a polyphosphate

Chemical Formula: HO7P2

Molecular Weight: 174.95 Daltons

Monoisotopic Molecular Weight: 177.9432255031 Daltons

diphosphate compound structure

SMILES: O=P(O)(OP([O-])([O-])=O)[O-]

InChI: InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-3

InChIKey: InChIKey=XPPKVPWEQAFLFU-UHFFFAOYSA-K

Unification Links: CAS:2466-09-3 , ChEBI:29888 , ChemSpider:996 , DrugBank:DB04160 , HMDB:HMDB00250 , IAF1260:33511 , KEGG:C00013 , MetaboLights:MTBLC33019 , PubChem:1023

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -480.93

Reactions known to consume the compound:

Not in pathways:
diphosphate + H2O → 2 phosphate + H+

Reactions known to produce the compound:

1,4-dihydroxy-2-naphthoate biosynthesis I :
ATP + 2-succinylbenzoate + coenzyme A → AMP + 4-(2'-carboxyphenyl)-4-oxobutyryl-CoA + diphosphate

2-methylcitrate cycle I :
propanoate + ATP + coenzyme A → propanoyl-CoA + AMP + diphosphate

5-aminoimidazole ribonucleotide biosynthesis I , 5-aminoimidazole ribonucleotide biosynthesis II , superpathway of 5-aminoimidazole ribonucleotide biosynthesis :
5-phospho-β-D-ribosylamine + L-glutamate + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + L-glutamine + H2O

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I :
7,8-dihydroneopterin 3'-triphosphate + H2O → 7,8-dihydroneopterin 3'-phosphate + diphosphate + H+

acetate conversion to acetyl-CoA :
acetate + ATP + coenzyme A → acetyl-CoA + AMP + diphosphate

adenine and adenosine salvage II :
AMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + adenine

adenine and adenosine salvage III :
IMP + diphosphate ← 5-phospho-α-D-ribose 1-diphosphate + hypoxanthine

adenosylcobalamin salvage from cobinamide I :
adenosyl-cobinamide phosphate + GTP + H+ → adenosylcobinamide-GDP + diphosphate

ADP-L-glycero-β-D-manno-heptose biosynthesis :
D-glycero-β-D-manno-heptose 1-phosphate + ATP + H+ → ADP-D-glycero-β-D-manno-heptose + diphosphate

anhydromuropeptides recycling , UDP-N-acetyl-D-glucosamine biosynthesis I :
N-acetyl-α-D-glucosamine 1-phosphate + UTP + H+ → UDP-N-acetyl-α-D-glucosamine + diphosphate

biotin-carboxyl carrier protein assembly :
a [biotin-carboxyl-carrier protein monomer] + biotin + ATP → AMP + a biotinylated [BCCP monomer] + diphosphate + H+

CDP-diacylglycerol biosynthesis I , CDP-diacylglycerol biosynthesis II :
CTP + a 1,2-diacyl-sn-glycerol 3-phosphate + H+ → a CDP-diacylglycerol + diphosphate

citrate lyase activation :
[a holo citrate lyase acyl-carrier protein] + acetate + ATP → an acetyl-[holo citrate lyase acyl-carrier protein] + AMP + diphosphate
2'-(5''-triphospho-α-D-ribosyl)-3'-dephospho-CoA + [a citrate-lyase acyl-carrier protein] → [a holo citrate lyase acyl-carrier protein] + diphosphate + H+

CMP-3-deoxy-D-manno-octulosonate biosynthesis I :
3-deoxy-D-manno-octulosonate + CTP → CMP-3-deoxy-α-D-manno-octulosonate + diphosphate

coenzyme A biosynthesis I :
4'-phosphopantetheine + ATP + H+ → 3'-dephospho-CoA + diphosphate
(R)-4'-phosphopantothenate + L-cysteine + CTP → CMP + R-4'-phosphopantothenoyl-L-cysteine + diphosphate + H+

cytidylyl molybdenum cofactor biosynthesis :
MoO2-molybdopterin cofactor + CTP + H+ → cytidylyl molybdenum cofactor + diphosphate

demethylmenaquinol-8 biosynthesis I :
all-trans-octaprenyl diphosphate + 1,4-dihydroxy-2-naphthoate + H+ → CO2 + demethylmenaquinol-8 + diphosphate

enterobactin biosynthesis :
ATP + 2,3-dihydroxybenzoate + H+ → 2,3-dihydroxybenzoyl adenylate + diphosphate

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acid + ATP + coenzyme A → a 2,3,4-saturated fatty acyl CoA + AMP + diphosphate

flavin biosynthesis I (bacteria and plants) :
GTP + 3 H2O → 2,5-diamino-6-(5-phospho-D-ribosylamino)pyrimidin-4(3H)-one + formate + diphosphate + 2 H+
ATP + FMN + H+ → FAD + diphosphate

galactose degradation I (Leloir pathway) , UDP-glucose biosynthesis :
α-D-glucose 1-phosphate + UTP + H+ → UDP-α-D-glucose + diphosphate

GDP-mannose biosynthesis :
α-D-mannose 1-phosphate + GTP + H+ → GDP-α-D-mannose + diphosphate

Reactions known to both consume and produce the compound:

dTDP-L-rhamnose biosynthesis I , dTDP-N-acetylthomosamine biosynthesis :
α-D-glucose 1-phosphate + dTTP + H+ ↔ dTDP-α-D-glucose + diphosphate

enterobactin biosynthesis :
L-serine + ATP + H+ ↔ L-seryl-adenylate + diphosphate

L-histidine biosynthesis :
1-(5-phospho-β-D-ribosyl)-ATP + diphosphate ↔ ATP + 5-phospho-α-D-ribose 1-diphosphate + H+

UMP biosynthesis :
orotidine 5'-phosphate + diphosphate ↔ 5-phospho-α-D-ribose 1-diphosphate + orotate

Not in pathways:
GTP ↔ cyclic-GMP + diphosphate
heme b + (2E,6E)-farnesyl diphosphate + H2O ↔ heme o + diphosphate

In Reactions of unknown directionality:

di-trans,poly-cis-undecaprenyl phosphate biosynthesis :
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = di-trans,octa-cis-undecaprenyl diphosphate + 8 diphosphate

Not in pathways:
ThiS protein + ATP = ThiS-COAMP + diphosphate
a deoxyribonucleoside triphosphate + (deoxynucleotides)(n) = (deoxynucleotides)(n+1) + diphosphate
ATP + an mRNA = an mRNA + diphosphate
ATP + ATP + H+ = 5',5'''-diadenosine tetraphosphate + diphosphate
a nucleoside triphosphate + RNA(n) = RNA(n+1) + diphosphate
protein chain elongation factor EF-P + D-β-lysine + ATP = protein chain elongation factor EF-P, β-lysyl-Lys34 + AMP + diphosphate
dimethylallyl diphosphate + an adenosine37 in tRNA = N6-dimethylallyladenosine37 in tRNA + diphosphate
initiator tRNAmet + L-methionine + ATP + H+ = an L-methionyl-[initiator tRNAmet] + AMP + diphosphate
carbamoyl-phosphate + ATP + H2O = O-carbamoyladenylate + diphosphate + phosphate

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

Activator (Mechanism unknown) of: glutaminase B [Prusiner76] , polyphosphate kinase [Comment 1]

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

Inhibitor (Competitive) of: xanthosine-5'-phosphate:L-glutamine amido-ligase (AMP-forming) [Spector75, Patel77] , pyruvate oxidase [Comment 2] , xanthosine-5'-phosphate:ammonia ligase (AMP-forming) [Spector75] , GTP cyclohydrolase [Foor75, Ritz01b] , pyrophosphohydrolase [OHandley96, Comment 3] , polyphosphate kinase [Comment 4] , adenine phosphoribosyltransferase [HochstadtOzer71, Comment 5] , methylglyoxal synthase [Hopper71, Hopper72, Comment 6]

Inhibitor (Noncompetitive) of: arginyl-tRNA synthetase [Charlier79] , methionine adenosyltransferase [Markham80] , quinolinate phosphoribosyltransferase (decarboxylating) [Bhatia96] , adenylate cyclase [Yang83a]

Inhibitor (Mechanism unknown) of: acetyl-CoA synthetase (AMP-forming) [Barak04a] , thiamine phosphate synthase [Kayama73, Kawasaki79] , glucose-1-phosphate adenylyltransferase [Preiss83] , galactarate dehydratase [Blumenthal66, Blumenthal64] , dTDP-glucose pyrophosphorylase [Zuccotti01, Comment 7] , α-dehydro-β-deoxy-D-glucarate aldolase [Fish66] , nucleoside diphosphate kinase [Roisin78] , dihydroneopterin triphosphate pyrophosphohydrolase [Suzuki74, Comment 8] , tRNA(i6A37) synthase [Rosenbaum72] , glutamine synthetase deadenylase [Shapiro69] , thiamin monophosphate kinase [Nishino72] , glutamine synthetase adenylyltransferase [Ebner70, Helmward89, Comment 9]

Inhibitor (Other types) of: aspartate ammonia-lyase

This compound has been characterized as an alternative substrate of the following enzymes: alkaline phosphatase

In Growth Media: PMA phosphorus source test + diphosphate


References

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Bernstein65: Bernstein R, Robbins P "Control aspects of uridine 5'-diphosphate glucose and thymidine 5'-diphosphate glucose synthesis by microbial enzymes." J Biol Chem 1965;240(1):391-397.

Bhatia96: Bhatia R, Calvo KC (1996). "The sequencing expression, purification, and steady-state kinetic analysis of quinolinate phosphoribosyl transferase from Escherichia coli." Arch Biochem Biophys 325(2);270-8. PMID: 8561507

Blumenthal64: Blumenthal HJ, Jepson T (1964). "Asymmetric dehydration of galactarate by bacterial galactarate dehydratase." Biochem Biophys Res Commun 1964;17(3);282-7. PMID: 4285952

Blumenthal66: Blumenthal, HJ, Jepson, T "Galactarate Dehydrase." Methods in Enzymology 9:665-669 (1966).

Charlier79: Charlier J, Gerlo E (1979). "Arginyl-tRNA synthetase from Escherichia coli K12. Purification, properties, and sequence of substrate addition." Biochemistry 18(14);3171-8. PMID: 37899

Cooper84: Cooper RA (1984). "Metabolism of methylglyoxal in microorganisms." Annu Rev Microbiol 1984;38;49-68. PMID: 6093685

Ebner70: Ebner E, Gancedo C, Holzer H "ATP:Glutamine synthetase adenylyltransferase (Escherichia coli B)." Methods in Enzymology 1970; 17A:922-927.

Ebner70a: Ebner E, Wolf D, Gancedo C, Elsasser S, Holzer H (1970). "ATP: glutamine synthetase adenylyltransferase from Escherichia coli B. Purification and properties." Eur J Biochem 1970;14(3);535-44. PMID: 4920894

Fish66: Fish D, Blumenthal H "2-keto-3-deoxy-D-glucarate aldolase." Meth Enz 1966;9:529-534.

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Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

HochstadtOzer71: Hochstadt-Ozer J, Stadtman ER (1971). "The regulation of purine utilization in bacteria. I. Purification of adenine phosphoribosyltransferase from Escherichia coli K12 and control of activity by nucleotides." J Biol Chem 246(17);5294-303. PMID: 4328693

Hopper71: Hopper DJ, Cooper RA (1971). "The regulation of Escherichia coli methylglyoxal synthase; a new control site in glycolysis?." FEBS Lett 13(4);213-216. PMID: 11945670

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Kawasaki79: Kawasaki T (1979). "Thiamine phosphate pyrophosphorylase." Methods Enzymol 1979;62;69-73. PMID: 374983

Kayama73: Kayama Y, Kawasaki T (1973). "Purification and properties of thiaminephosphate pyrophosphorylase of Escherichia coli." Arch Biochem Biophys 1973;158(1);242-8. PMID: 4580841

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Nishino72: Nishino H (1972). "Biogenesis of cocarboxylase in Escherichia coli. Partial purification and some properties of thiamine monophosphate kinase." J Biochem (Tokyo) 1972;72(5);1093-100. PMID: 4567662

OHandley96: O'Handley SF, Frick DN, Bullions LC, Mildvan AS, Bessman MJ (1996). "Escherichia coli orf17 codes for a nucleoside triphosphate pyrophosphohydrolase member of the MutT family of proteins. Cloning, purification, and characterization of the enzyme." J Biol Chem 1996;271(40);24649-54. PMID: 8798731

Patel77: Patel N, Moyed HS, Kane JF (1977). "Properties of xanthosine 5'-monophosphate-amidotransferase from Escherichia coli." Arch Biochem Biophys 1977;178(2);652-61. PMID: 189701

Preiss83: Preiss J, Greenberg E (1983). "Pyrophosphate may be involved in regulation of bacterial glycogen synthesis." Biochem Biophys Res Commun 115(3);820-6. PMID: 6312996

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

Ritz01b: Ritz H, Schramek N, Bracher A, Herz S, Eisenreich W, Richter G, Bacher A (2001). "Biosynthesis of riboflavin: studies on the mechanism of GTP cyclohydrolase II." J Biol Chem 276(25);22273-7. PMID: 11301327

Roisin78: Roisin MP, Kepes A (1978). "Nucleosidediphosphate kinase of Escherichia coli, a periplasmic enzyme." Biochim Biophys Acta 1978;526(2);418-28. PMID: 214126

Rosenbaum72: Rosenbaum N, Gefter ML (1972). "Delta 2 -isopentenylpyrophosphate: transfer ribonucleic acid 2 -isopentenyltransferase from Escherichia coli. Purification and properties of the enzyme." J Biol Chem 247(18);5675-80. PMID: 4341485

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Spector75: Spector T, Beacham LM (1975). "Guanosine monophosphate synthetase from Escherichia coli B-96. Inhibition by nucleosides." J Biol Chem 250(8);3101-7. PMID: 164459

Suzuki74: Suzuki Y, Brown GM (1974). "The biosynthesis of folic acid. XII. Purification and properties of dihydroneopterin triphosphate pyrophosphohydrolase." J Biol Chem 1974;249(8);2405-10. PMID: 4362677

Tzeng00: Tzeng CM, Kornberg A (2000). "The multiple activities of polyphosphate kinase of Escherichia coli and their subunit structure determined by radiation target analysis." J Biol Chem 2000;275(6);3977-83. PMID: 10660553

Yang83a: Yang JK, Epstein W (1983). "Purification and characterization of adenylate cyclase from Escherichia coli K12." J Biol Chem 1983;258(6);3750-8. PMID: 6300054

Zuccotti01: Zuccotti S, Zanardi D, Rosano C, Sturla L, Tonetti M, Bolognesi M (2001). "Kinetic and crystallographic analyses support a sequential-ordered bi bi catalytic mechanism for Escherichia coli glucose-1-phosphate thymidylyltransferase." J Mol Biol 313(4);831-43. PMID: 11697907


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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