Glycolaldehyde

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Glycolaldehyde

IUPAC name	2-Hydroxyethanal
Identifiers
CAS number	[141-46-8]
Properties
Molecular formula	C₂H₄O₂
Molar mass	60.052 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Glycolaldehyde (HOCH₂-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). It has an aldehyde and a hydroxyl group, and is the smallest possible molecule to bear both of these functionalities. 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.