Efficient desymmetrization of 4,6-di-O-benzyl-myo-inositol by Lipozyme TL-IM

Carbohydr Res. 2014 Mar 11:386:7-11. doi: 10.1016/j.carres.2013.11.005. Epub 2013 Nov 23.

Abstract

The enantioselective enzymatic desymmetrization of 4,6-di-O-benzyl-myo-inositol, a myo-inositol derivative, was effectively catalyzed by Thermomyces lanuginosus lipase (TL-IM). The product 1D-1-O-acetyl-4,6-di-O-benzyl-myo-inositol, a useful precursor to inositol phosphates, was obtained in excellent yield and enantiomeric excess. Through the investigation of the effects of solvent, biocatalyst load, and temperature, a more economical procedure resulted. The feasibility of biocatalyst reuse was also shown.

Keywords: Chiral; Desymmetrization; Enantioselectivity; Inositol; TL-IM Lipase; Thermomyces lanuginosus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / enzymology*
  • Benzyl Compounds / chemistry*
  • Biocatalysis
  • Fungal Proteins / chemistry*
  • Inositol / analogs & derivatives*
  • Inositol / chemistry
  • Kinetics
  • Lipase / chemistry*
  • Stereoisomerism

Substances

  • 4,6-di-O-benzyl-myo-inositol
  • Benzyl Compounds
  • Fungal Proteins
  • Inositol
  • Lipozyme
  • Lipase