title: Formation of glycolaldehyde phosphate from glycolaldehyde in aqueous solution.
abstract: Amidotriphosphate (0.1 M) in aqueous solution at near neutral pH in the presence of magnesium ions (0.25 M) converts glycolaldehyde (0.025 M) within days at room temperature into glycolaldehyde phosphate in (analytically) nearly quantitative yields (76% in isolated product). This robust phosphorylation process was observed to proceed at concentrations as low as 30 microM glycolaldehyde and 60 microM phosphorylation reagent under otherwise identical conditions. In sharp contrast, attempts to achieve a phosphorylation of glycolaldehyde with cyclotriphosphate ('trimetaphosphate') as phosphorylating reagent were unsuccessful. Mechanistically, the phosphorylation of glycolaldehyde with amidotriphosphate is an example of intramolecular delivery of the phosphate group.
authors.affiliation: Skaggs Institute for Chemical Biology, Scripps Research Institute (TSRI), La Jolla, CA 92037, USA.
authors.forename: R
authors.initials: R
authors.lastname: Krishnamurthy
authors.forename: G
authors.initials: G
authors.lastname: Arrhenius
authors.forename: A
authors.initials: A
authors.lastname: Eschenmoser
mesh_terms: D000079:Acetaldehyde / Q000031:analogs & derivatives* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010766:Phosphorylation; D012996:Solutions
chemical_list: D012996:Solutions; C001308:glycolaldehyde phosphate; D000079:Acetaldehyde; C010972:glycolaldehyde