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Escherichia coli K-12 substr. MG1655 Compound: glycolaldehyde

Synonyms: glycoaldehyde, 2-OH-acetaldehyde, hydroxyacetaldehyde, 2-hydroxyethanal

Superclasses: all carbohydratesa carbohydratea glycana sugara monosaccharidean aldosean aldodiose
an aldehyde or ketonean aldehyde
an aldehyde or ketonean aldehydean aldosean aldodiose


Chemical Formula: C2H4O2

Molecular Weight: 60.052 Daltons

Monoisotopic Molecular Weight: 60.0211293726 Daltons

glycolaldehyde compound structure

SMILES: C(O)[CH]=O

InChI: InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2

InChIKey: InChIKey=WGCNASOHLSPBMP-UHFFFAOYSA-N

Unification Links: CAS:141-46-8, ChEBI:17071, ChemSpider:736, HMDB:HMDB03344, IAF1260:34446, KEGG:C00266, MetaboLights:MTBLC17071, PubChem:756

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -70.28

Reactions known to consume the compound:

D-arabinose degradation I , ethylene glycol degradation :
glycolaldehyde + NAD+ + H2O → glycolate + NADH + 2 H+

Not in pathways:
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+

Reactions known to produce the compound:

6-hydroxymethyl-dihydropterin diphosphate biosynthesis I :
7,8-dihydroneopterin → glycolaldehyde + 6-hydroxymethyl-7,8-dihydropterin

Not in pathways:
isethionate + FMNH2 + oxygen → glycolaldehyde + sulfite + FMN + H2O + 2 H+

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

two-component alkanesulfonate monooxygenase :
an alkylsulfonate + FMNH2 + oxygen → an aldehyde + sulfite + FMN + H2O + 2 H+

Not in pathways:
an aliphatic amine[periplasm] + H2O[periplasm] + oxygen[periplasm]an aldehyde[periplasm] + ammonium[periplasm] + hydrogen peroxide[periplasm]
a primary amine[periplasm] + H2O[periplasm] + oxygen[periplasm]an aldehyde[periplasm] + ammonium[periplasm] + hydrogen peroxide[periplasm]

Reactions known to both consume and produce the compound:

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

ethylene glycol degradation :
ethylene glycol + NAD+glycolaldehyde + NADH + H+

Not in pathways:
4-hydroxy-L-threonine ↔ glycolaldehyde + glycine

Not in pathways:
a primary alcohol + NAD+an aldehyde + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
2-dehydro-3-deoxy-D-arabinonate = glycolaldehyde + pyruvate

Not in pathways:
an aldose[periplasm] + an oxidized unknown electron acceptor[periplasm] + H2O[periplasm] = an aldonate[periplasm] + an reduced unknown electron acceptor[periplasm] + H+[periplasm]

Not in pathways:
an aldehyde[periplasm] + FAD[periplasm] + H2O[periplasm] = a carboxylate[periplasm] + FADH2[periplasm]
an alcohol + NADP+ = an aldehyde + NADPH + H+

In Transport reactions:
a monosaccharide[periplasm]a monosaccharide[extracellular space],
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasm] → a [PTS enzyme I]-L-histidine + a sugar phosphate[cytosol]

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

Inhibitor (Mechanism unknown) of: glycolaldehyde dehydrogenase [Baldoma87]

This compound has been characterized as an alternative substrate of the following enzymes: lactaldehyde dehydrogenase, rhamnulose-1-phosphate aldolase, aldehyde reductase, L-fuculose-phosphate aldolase, methylglyoxal reductase, methylglyoxal reductase (NADPH-dependent), 2-oxo-3-deoxygalactonate 6-phosphate aldolase


References

Baldoma87: Baldoma L, Aguilar J (1987). "Involvement of lactaldehyde dehydrogenase in several metabolic pathways of Escherichia coli K12." J Biol Chem 262(29);13991-6. PMID: 3308886


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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 Pathway Tools version 19.5 (software by SRI International) on Fri Apr 29, 2016, biocyc11.