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

研究成果: Article

12 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)197-200
ページ数4
ジャーナルJournal of Molecular Catalysis B: Enzymatic
59
発行部数1-3
DOI
出版物ステータスPublished - 2009 7

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

ASJC Scopus subject areas

  • Biochemistry
  • Bioengineering
  • Catalysis
  • Process Chemistry and Technology

これを引用

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.

:: Journal of Molecular Catalysis B: Enzymatic, 巻 59, 番号 1-3, 07.2009, p. 197-200.

研究成果: Article

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. :: Journal of Molecular Catalysis B: Enzymatic. 2009 ; 巻 59, 番号 1-3. pp. 197-200.
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AU - Sugai, Takeshi

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KW - d-Lyxose

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KW - l-Ribose

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