A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose

Kazunori Kitsuda, Jordi Calveras, Yasuhito Nagai, Toshinori Higashi, Takeshi Sugai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A new chemo-enzymatic route to tetra-O-acetyl-l-ribofuranose from d-lyxose is described. Lipase-catalyzed regioselective transesterification of acetate proceeded on C-4 of the d-lyxopyranoside. Subsequently, stereochemistry of liberated secondary alcohol was inverted by way of oxidation and reduction by IBX and NaBH(OAc)3 to give l-ribopyranoside. After deprotection, the furanose-pyranose isomeric mixture was converged to the target molecule, taking advantage of lipase-catalyzed preferential acetylation of primary alcohol on C-5.

Original languageEnglish
Pages (from-to)197-200
Number of pages4
JournalJournal of Molecular Catalysis B: Enzymatic
Volume59
Issue number1-3
DOIs
Publication statusPublished - 2009 Jul 1

Keywords

  • Lipase
  • Regioselective reaction
  • Stereochemical inversion
  • d-Lyxose
  • l-Nucleoside
  • l-Ribose

ASJC Scopus subject areas

  • Catalysis
  • Bioengineering
  • Biochemistry
  • Process Chemistry and Technology

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