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Glycolaldehyde - Wikipedia, the free encyclopedia

Glycolaldehyde

From Wikipedia, the free encyclopedia

Glycolaldehyde
Glycolaldehyde
Systematic name 2-Hydroxyethanal
Chemical formula C2H4O2
Molecular mass xx.xx g/mol
Density x.xxx g/cm3
Melting point xx.x °C
Boiling point xx.x °C
CAS number [xx-xx-xx]
SMILES OCC=O
Disclaimer and references

Glycolaldehyde (HOCH2-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). Glycolaldehyde is readily converted to acetyl coenzyme A. It has an aldehyde and a hydroxyl group. However, it is not actually a sugar, because there is only one hydroxyl group. Glycolaldehyde is formed from many sources, including the amino acid glycine and from purone catabolism. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamin pyrophosphate during the pentose phosphate shunt.

[edit] Formation

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" (the compound is an intermediate in the Formose reaction).

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.

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