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

doi:10.1016/j.molcatb.2009.02.014

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

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	197-200
Number of pages	4
Journal	Journal of Molecular Catalysis B: Enzymatic
Volume	59
Issue number	1-3
DOIs	https://doi.org/10.1016/j.molcatb.2009.02.014
Publication status	Published - 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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title = "A short-step chemo-enzymatic synthesis of a precursor for l-nucleosides from d-lyxose",

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.",

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AU - Kitsuda, Kazunori

AU - Calveras, Jordi

AU - Nagai, Yasuhito

AU - Higashi, Toshinori

AU - Sugai, Takeshi

PY - 2009/7/1

Y1 - 2009/7/1

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KW - Lipase

KW - Regioselective reaction

KW - Stereochemical inversion

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KW - l-Nucleoside

KW - l-Ribose

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