Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):547-57. doi: 10.1081/NCN-120021954.

Abstract

The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: beta-D-ribo-, beta-D-deoxyribo-, and beta-D-dideoxyribonucleosides. The method developed for the latter class permitted access to a novel bicyclo[3.1.0]hexene-type nucleosides structurally similar to D4T and carbovir. A structural analysis and biological activities are discussed.

Publication types

  • Review

MeSH terms

  • Deoxyribonucleosides / chemical synthesis
  • Deoxyribonucleosides / chemistry
  • Indicators and Reagents
  • Kinetics
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Deoxyribonucleosides
  • Indicators and Reagents
  • Nucleosides