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

Yongseok Choi, Hyung R. Moon, Yuichi Yoshimura, Victor E. Marquez

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

The present work describes some recent approaches to the syntheses of three classes of locked-North nucleosides: β-D-ribo-, β-D-deoxyribo-, and β-D-dideoxy-ribonucleosides. 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.

Original languageEnglish
Pages (from-to)547-557
Number of pages11
JournalNucleosides, Nucleotides and Nucleic Acids
Volume22
Issue number5-8
DOIs
Publication statusPublished - 2003
Externally publishedYes

Keywords

  • Bicyclo[3.1.0]hexane and bicyclo[3.1.0]hexene
  • Conformationally locked carbocyclic nucleosides
  • D4T and carbovir analogues
  • Intramolecular cyclopropanation
  • Lipase-catalyzed resolution
  • Pseudorotational analysis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Genetics

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