Glycolaldehyde

Glycolaldehyde

chembox new
Name = Glycolaldehyde
ImageFile = Glycolaldehyde.pngImageSize = 120px
ImageName = Glycolaldehyde
IUPACName = 2-hydroxyacetaldehyde
Section1 = Chembox Identifiers
CASNo = 141-46-8
ChemSpiderID = 736
SMILES = O=CCO
Section2 = Chembox Properties
Formula = C2H4O2
MolarMass = 60.052 g/mol
Density =
MeltingPt =
BoilingPt =

Glycolaldehyde (HOCH2-CH=O) is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is the only possible diose, a 2-carbon monosaccharide, although a diose is not strictly a saccharide.

Formation

Glycolaldehyde is an intermediate in the formose reaction.

Glycolaldehyde forms from many precursors, including the amino acid glycine. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamine pyrophosphate during the pentose phosphate shunt.

In purine catabolism, xanthine is first converted to urate. This is converted to 5-hydroxyisourate, which decarboxylates to allantoin and allantoic acid. After hydrolyzing one urea, this leaves glycolureate. After hydrolyzing the second urea, glycolaldehyde is left. Two glycolaldehydes condense to form erythrose 4-phosphate, which goes to the pentose phosphate shunt again.

Glycolaldehyde was identified in many other planets and also at the middle of the Milky Way. Although technically not sugar, the discovery of interplanetary glycolaldehyde has been reported in many publications as "sugar found in space".

External links

*cite news | title=Cold Sugar in Space Provides Clue to the Molecular Origin of Life | publisher=National Radio Astronomy Observatory | date=September 20, 2004 | url=http://www.nrao.edu/pr/2004/coldsugar/ | accessdate=2006-12-20


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