Synthesis of conformationally locked carbocyclic nucleoside phosphonates to probe the active site of HIV-1 RT

Nucleic Acids Symp Ser (Oxf). 2008:(52):623-4. doi: 10.1093/nass/nrn315.

Abstract

The conformationally locked carbocyclic nucleoside phosphonates 2 and 2' and key intermediates for the synthesis of 3 and 3' were prepared from a chiral cyclopentene derivative and epicholorohydrine, respectively. The structure of the nucleoside precursor 6 was confirmed by X-ray crystallography. These carbocyclic nucleoside phosphonates were designed to probe their binding interactions at the active site of HIV-1-RT.

Publication types

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

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine / chemistry
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Catalytic Domain
  • HIV Reverse Transcriptase / drug effects*
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Reverse Transcriptase Inhibitors / chemical synthesis*
  • Reverse Transcriptase Inhibitors / chemistry

Substances

  • Anti-HIV Agents
  • Organophosphonates
  • Reverse Transcriptase Inhibitors
  • reverse transcriptase, Human immunodeficiency virus 1
  • HIV Reverse Transcriptase
  • Adenosine