Lipase-catalyzed regioselective one-step synthesis of penta- O-acetyl-3-hydroxylactal

Marco Filice, Renzo Vanna, Marco Terreni, Jose M. Guisan, Jose M. Palomo

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A highly efficient regioselective enzymatic preparation of penta-O-acetyl-1.,5-anhydro-2-deoxy-3-hydroxy-4-O-ß-galactopyranosyl-D- arabinohex-1-enitol has been successfully performed for the first time. This product was obtained in >99% conversion (>95 % overall yield) by hydrolysis of perO-acetylated lactal catalyzed by the lipase from. Rhizomucor miehei immobilized on octylagarose. This molecule could be a potential building block for efficient synthesis of oligosaccharides or glycoconjugates.

Original languageEnglish
Pages (from-to)3327-3329
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
Publication statusPublished - Jul 2009

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Glycoconjugates
Lipase
Oligosaccharides
hydrolysis
Hydrolysis
preparation
Molecules
synthesis
products
molecules

Keywords

  • Carbohydrates /
  • Enzyme catalysis
  • Hydrolysis /
  • Regioselectivity /
  • Supported catalysts /

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Lipase-catalyzed regioselective one-step synthesis of penta- O-acetyl-3-hydroxylactal. / Filice, Marco; Vanna, Renzo; Terreni, Marco; Guisan, Jose M.; Palomo, Jose M.

In: European Journal of Organic Chemistry, No. 20, 07.2009, p. 3327-3329.

Research output: Contribution to journalArticle

Filice, Marco ; Vanna, Renzo ; Terreni, Marco ; Guisan, Jose M. ; Palomo, Jose M. / Lipase-catalyzed regioselective one-step synthesis of penta- O-acetyl-3-hydroxylactal. In: European Journal of Organic Chemistry. 2009 ; No. 20. pp. 3327-3329.
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