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

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

Marcela G Vasconcelos  1 , Raissa H C Briggs  1 , Lucia C S Aguiar  2 , Denise M G Freire  3 , Alessandro B C Simas  4
Affiliations

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

Marcela G Vasconcelos et al. Carbohydr Res. .

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.

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