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Origins of life and evolution of the biosphere

, Volume 29, Issue 4, pp 333–354 | Cite as

Formation of Glycolaldehyde Phosphate from Glycolaldehyde in Aqueous Solution

  • Ramanarayanan Krishnamurthy
  • Gustaf Arrhenius
  • Albert Eschenmoser
Article

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 μM glycolaldehyde and 60 μM 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.

Keywords

Phosphate Aqueous Solution Magnesium Organic Chemistry Geochemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Kluwer Academic Publishers 1999

Authors and Affiliations

  • Ramanarayanan Krishnamurthy
    • 1
  • Gustaf Arrhenius
    • 2
  • Albert Eschenmoser
    • 1
    • 3
  1. 1.The Skaggs Institute for Chemical BiologyThe Scripps Research Institute (TSRI)La JollaU.S.A.
  2. 2.Scripps Institution of Oceanography (SIO)University of California San DiegoLa JollaU.S.A.
  3. 3.Laboratory of Organic ChemistrySwiss Federal Institute of Technology (ETH)ZürichSwitzerland

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