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Escherichia coli K-12 substr. MG1655 Compound: glycolaldehyde

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

Superclasses: all carbohydrates a carbohydrate a glycan a sugar a monosaccharide an aldose an aldodiose
an aldehyde or ketone an aldehyde an aldose an aldodiose
an aldehyde or ketone an aldehyde

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 Change 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[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space]an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]
a primary amine[periplasmic space] + H2O[periplasmic space] + oxygen[periplasmic space]an aldehyde[periplasmic space] + ammonium[periplasmic space] + hydrogen peroxide[periplasmic space]

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[periplasmic space] + an unknown oxidized electron acceptor[periplasmic space] + H2O[periplasmic space] = an aldonate[periplasmic space] + an unknown reduced electron acceptor[periplasmic space] + H+[periplasmic space]

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

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[periplasmic space] → 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: methylglyoxal reductase , L-fuculose-phosphate aldolase , 2-oxo-3-deoxygalactonate 6-phosphate aldolase , aldehyde reductase , rhamnulose-1-phosphate aldolase , lactaldehyde dehydrogenase , methylglyoxal reductase (NADPH-dependent)


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 SRI International Pathway Tools version 19.0 on Mon Mar 30, 2015, BIOCYC14B.