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 journal › Article

12 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

Fingerprint

Lipases
Lipase
Nucleosides
Alcohols
Acetylation
Stereochemistry
Transesterification
Oxidation-Reduction
Acetates
Oxidation
Molecules
lyxose

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Bioengineering
  • Catalysis
  • Process Chemistry and Technology

Cite this

A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose. / Kitsuda, Kazunori; Calveras, Jordi; Nagai, Yasuhito; Higashi, Toshinori; Sugai, Takeshi.

In: Journal of Molecular Catalysis B: Enzymatic, Vol. 59, No. 1-3, 07.2009, p. 197-200.

Research output: Contribution to journal › Article

Kitsuda, K, Calveras, J, Nagai, Y, Higashi, T & Sugai, T 2009, 'A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose', Journal of Molecular Catalysis B: Enzymatic, vol. 59, no. 1-3, pp. 197-200. https://doi.org/10.1016/j.molcatb.2009.02.014
Kitsuda K, Calveras J, Nagai Y, Higashi T, Sugai T. A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose. Journal of Molecular Catalysis B: Enzymatic. 2009 Jul;59(1-3):197-200. https://doi.org/10.1016/j.molcatb.2009.02.014
Kitsuda, Kazunori ; Calveras, Jordi ; Nagai, Yasuhito ; Higashi, Toshinori ; Sugai, Takeshi. / A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose. In: Journal of Molecular Catalysis B: Enzymatic. 2009 ; Vol. 59, No. 1-3. pp. 197-200.
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