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

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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Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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