Remarkable acceleration for the deamination of carbocyclic purine nucleosides by adenosine deaminase under high-pressure

Nucleic Acids Symp Ser. 1993:(29):95-6.

Abstract

Deamination of an anti-HIV carbocyclic adenine nucleoside, 9-[c-4,t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine [(+/-)-BCA] and (+/-)-diamino-carbovir by adenosine deaminase under high-pressure (4 kbar) was carried out. Deamination of the former gave the corresponding (-)-hypoxanthine derivative whereas that of the latter produced (-)-carbovir having anti-HIV activity. The enantiomeric excess (e.e.) of both products was nearly 100%.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemistry
  • Adenosine Deaminase / chemistry*
  • Antiviral Agents / chemistry*
  • Cyclopentanes / chemistry*
  • Deamination
  • Dideoxynucleosides / chemistry
  • HIV
  • Pressure
  • Stereoisomerism

Substances

  • Antiviral Agents
  • Cyclopentanes
  • Dideoxynucleosides
  • carbovir
  • 9-(4,5-bishydroxymethylcyclopent-2-en-1-yl)-9H-adenine
  • Adenosine Deaminase
  • Adenine