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Escherichia coli K-12 substr. MG1655 Compound: glycerone phosphate

Abbrev Name: DHAP

Synonyms: DHAP, dihydroxyacetone phosphate, dihydroxyacetone-P, di-OH-acetone-P, dihydroxy-acetone phosphate, 3-hydroxy-2-oxopropyl phosphate

Chemical Formula: C3H5O6P

Molecular Weight: 168.04 Daltons

Monoisotopic Molecular Weight: 169.9980244673 Daltons

glycerone phosphate compound structure

SMILES: C(C(=O)CO)OP([O-])([O-])=O

InChI: InChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)/p-2

InChIKey: InChIKey=GNGACRATGGDKBX-UHFFFAOYSA-L

Unification Links: CAS:57-04-5 , ChEBI:57642 , ChemSpider:3833110 , HMDB:HMDB01473 , IAF1260:33898 , KEGG:C00111 , MetaboLights:MTBLC57642 , PubChem:4643300

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -317.59

Reactions known to consume the compound:

CDP-diacylglycerol biosynthesis I , CDP-diacylglycerol biosynthesis II :
sn-glycerol 3-phosphate + NAD(P)+glycerone phosphate + NAD(P)H + H+

NAD biosynthesis I (from aspartate) :
2-iminosuccinate + glycerone phosphate → quinolinate + phosphate + 2 H2O

Not in pathways:
glycerone phosphate → methylglyoxal + phosphate

Reactions known to produce the compound:

autoinducer AI-2 degradation :
glycerone phosphate + acetyl-CoA ← 3-hydroxy-5-phosphonooxypentane-2,4-dione + coenzyme A

glycerol degradation I :
sn-glycerol 3-phosphate + a ubiquinone[inner membrane]glycerone phosphate + an ubiquinol[inner membrane]
sn-glycerol 3-phosphate + a menaquinone[inner membrane]glycerone phosphate + a menaquinol[inner membrane]

glycerol degradation V :
dihydroxyacetone + phosphoenolpyruvate → glycerone phosphate + pyruvate

glycerol-3-phosphate to cytochrome bo oxidase electron transfer , nitrate reduction X (periplasmic, dissimilatory) :
sn-glycerol 3-phosphate + a ubiquinone[inner membrane]glycerone phosphate + an ubiquinol[inner membrane]

glycerol-3-phosphate to fumarate electron transfer , nitrate reduction IX (dissimilatory) :
sn-glycerol 3-phosphate + a menaquinone[inner membrane]glycerone phosphate + a menaquinol[inner membrane]

glycerophosphodiester degradation :
sn-glycerol 3-phosphate + a ubiquinone[inner membrane]glycerone phosphate + an ubiquinol[inner membrane]
sn-glycerol 3-phosphate + a menaquinone[inner membrane]glycerone phosphate + a menaquinol[inner membrane]

sedoheptulose bisphosphate bypass :
glycerone phosphate + D-erythrose 4-phosphate ← D-sedoheptulose-1,7-bisphosphate

sulfoglycolysis :
6-deoxy-6-sulfo-D-fructose 1-phosphate → sulfolactaldehyde + glycerone phosphate

Reactions known to both consume and produce the compound:

D-arabinose degradation I :
D-ribulose 1-phosphate ↔ glycolaldehyde + glycerone phosphate

fucose degradation :
L-fuculose 1-phosphate ↔ (S)-lactaldehyde + glycerone phosphate

galactitol degradation :
D-tagatofuranose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate

gluconeogenesis I :
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate

glycolysis I (from glucose 6-phosphate) :
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate

glycolysis II (from fructose 6-phosphate) :
fructose 1,6-bisphosphate ↔ glycerone phosphate + D-glyceraldehyde 3-phosphate
D-glyceraldehyde 3-phosphate ↔ glycerone phosphate

L-rhamnose degradation I :
L-rhamnulose 1-phosphate ↔ (S)-lactaldehyde + glycerone phosphate

In Redox half-reactions:
glycerone phosphate[in] + 2 H+[in] + 2 e-[membrane]sn-glycerol 3-phosphate[in]

Enzymes activated by glycerone phosphate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: methylglyoxal synthase [Comment 1]

Enzymes inhibited by glycerone phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glycerol-3-phosphate dehydrogenase, aerobic [Schryvers78]

This compound has been characterized as an alternative substrate of the following enzymes: acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase , deoxyribose-phosphate aldolase


References

Schryvers78: Schryvers A, Lohmeier E, Weiner JH (1978). "Chemical and functional properties of the native and reconstituted forms of the membrane-bound, aerobic glycerol-3-phosphate dehydrogenase of Escherichia coli." J Biol Chem 253(3);783-8. PMID: 340460

Totemeyer98: Totemeyer S, Booth NA, Nichols WW, Dunbar B, Booth IR (1998). "From famine to feast: the role of methylglyoxal production in Escherichia coli." Mol Microbiol 1998;27(3);553-62. PMID: 9489667


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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.0 on Fri Sep 4, 2015, biocyc14.