MetaCyc Compound: 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate

Synonyms: glucosyl-3-phsophoglycerate, 2-(α-D-glucopyranosyl)-3-phospho-D-glycerate

Superclasses: a glycerate

Citations: [Costa06]

Chemical Formula: C9H14O12P

Molecular Weight: 345.18 Daltons

Monoisotopic Molecular Weight: 348.0457625209 Daltons

2-<i>O</i>-(α-D-glucopyranosyl)-3-phospho-D-glycerate compound structure

SMILES: C(C(C([O-])=O)OC1(C(C(C(C(O1)CO)O)O)O))OP([O-])([O-])=O

InChI: InChI=1S/C9H17O12P/c10-1-3-5(11)6(12)7(13)9(20-3)21-4(8(14)15)2-19-22(16,17)18/h3-7,9-13H,1-2H2,(H,14,15)(H2,16,17,18)/p-3/t3-,4-,5-,6+,7-,9-/m1/s1


Unification Links: ChEBI:62600, PubChem:25201949

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -389.39285Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

glucosylglycerate biosynthesis I :
2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + H2O → 2-O-(α-D-glucopyranosyl)-D-glycerate + phosphate

mannosylglucosylglycerate biosynthesis I :
GDP-α-D-mannose + 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate → GDP + 2-[2-O-(α-D-mannopyranosyl)-(1→2)-α-D-glucopyranosyl]-3-phospho-D-glycerate + H+

Reactions known to produce the compound:

glucosylglycerate biosynthesis I :
GDP-α-D-glucose + 3-phospho-D-glycerate → 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + GDP + H+

mannosylglucosylglycerate biosynthesis I :
UDP-α-D-glucose + 3-phospho-D-glycerate → 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + UDP + H+

In Reactions of unknown directionality:

Not in pathways:
an NDP-α-D-glucose + 3-phospho-D-glycerate = 2-O-(α-D-glucopyranosyl)-3-phospho-D-glycerate + a nucleoside diphosphate + H+

This compound has been characterized as an alternative substrate of the following enzymes: glucosyl-3-phosphoglycerate phosphatase


Costa06: Costa J, Empadinhas N, Goncalves L, Lamosa P, Santos H, da Costa MS (2006). "Characterization of the biosynthetic pathway of glucosylglycerate in the archaeon Methanococcoides burtonii." J Bacteriol 188(3);1022-30. PMID: 16428406

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

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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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