Formation of Glycolaldehyde Phosphate from Glycolaldehyde in Aqueous Solution |
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Authors: | Krishnamurthy Ramanarayanan Arrhenius Gustaf Eschenmoser Albert |
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Affiliation: | (1) The Skaggs Institute for Chemical Biology, The Scripps Research Institute (TSRI), La Jolla, CA, 92037, U.S.A.;(2) Scripps Institution of Oceanography (SIO), University of California San Diego, La Jolla, CA, 92093-0220, U.S.A.;(3) Laboratory of Organic Chemistry, Swiss Federal Institute of Technology (ETH), Universitätstrasse 16, CH-8092 Zürich, Switzerland |
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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 M glycolaldehyde and 60 M 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. |
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