The triphosphate of beta-D-4'-C-ethynyl-2',3'-dideoxycytidine is the preferred enantiomer substrate for HIV reverse transcriptase

Bioorg Med Chem. 2007 Jan 1;15(1):283-7. doi: 10.1016/j.bmc.2006.09.061. Epub 2006 Sep 29.

Abstract

The enantioselective synthesis of the beta-d (1) enantiomer of 4'-C-ethynyl-2',3'-dideoxycytidine confirms an earlier stereochemical assignment that was strictly based on the ability of HIV reverse transcriptase and its M184V mutant to discriminate between the d- and l-configuration of nucleoside 5'-triphosphates.

Publication types

  • Research Support, N.I.H., Intramural

MeSH terms

  • HIV Reverse Transcriptase / chemistry*
  • Molecular Structure
  • Nucleosides / chemistry
  • Polyphosphates / chemistry*
  • Reverse Transcriptase Inhibitors / chemical synthesis
  • Reverse Transcriptase Inhibitors / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Substrate Specificity
  • Zalcitabine / analogs & derivatives*
  • Zalcitabine / chemical synthesis
  • Zalcitabine / chemistry

Substances

  • Nucleosides
  • Polyphosphates
  • Reverse Transcriptase Inhibitors
  • beta-D-4'-C-ethynyl-2',3'-dideoxycytidine
  • Zalcitabine
  • HIV Reverse Transcriptase
  • triphosphoric acid