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Related Experiment Videos

Formate ester formation in amide solutions.

A M Schoffstall1, S M Mahone

  • 1Department of Chemistry, University of Colorado at Colorado Springs 80907, USA.

Origins of Life and Evolution of the Biosphere : the Journal of the International Society for the Study of the Origin of Life
|January 1, 1988
PubMed
Summary

Formate esters form from alcohols and nucleosides in formamide at high temperatures. These esters do not intermediate in phosphorylation reactions, but rather represent a side reaction during nucleoside phosphorylation in formamide.

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Nucleoside and deoxynucleoside phosphorylation in formamide solutions.

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Area of Science:

  • Organic Chemistry
  • Biochemistry

Background:

  • Formamide is a common solvent used in phosphorylation reactions.
  • The potential role of formate esters as intermediates in these reactions is not fully understood.

Purpose of the Study:

  • To investigate the formation and reactivity of formate esters in formamide.
  • To determine if formate esters are intermediates in the phosphorylation of nucleosides.

Main Methods:

  • Reaction of alcohols, deoxynucleosides, and nucleosides with formamide at elevated temperatures (100-130°C).
  • Hydrolysis of formate esters in aqueous solution.
  • Testing the reactivity of formate esters with hydrogen phosphate ion.

Main Results:

  • Formate esters are formed from alcohols and nucleosides in formamide, with faster formation at 130°C.

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  • Formate esters readily hydrolyze in aqueous solution.
  • Formate esters do not react with hydrogen phosphate ion.

    • Conclusions:

    • Formate esters are not intermediates in the phosphorylation of nucleosides in formamide.
    • The formation of formate esters is a side reaction during nucleoside phosphorylation in formamide.