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 journalArticle

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 Sep 29
Externally publishedYes

Fingerprint

carbovir
Nucleosides
Stavudine
Ribonucleosides
Bioactivity
Structural analysis
1-hexene

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

  • Genetics
  • Biochemistry

Cite this

Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets. / Choi, Yongseok; Moon, Hyung R.; Yoshimura, Yuichi; Marquez, Victor E.

In: Nucleosides, Nucleotides and Nucleic Acids, Vol. 22, No. 5-8, 29.09.2003, p. 547-557.

Research output: Contribution to journalArticle

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