Selective lipase-catalyzed preparation of diol monobenzoates by transesterification and alcoholysis reactions in organic solvents

Lipases from Mucor miehei (MML) and Candida antarctica (CAL) are able to catalyze the monobenzoylation of the primary hydroxy group of 1,2- 1,4- or 1,5-diols with vinyl benzoate in an organic solvent, the reaction proceeding with high regioselectivity and moderate enantioselectivity. The lipase-cata...

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Bibliographic Details
Published in:Journal of Molecular Catalysis B: Enzymatic
Main Authors: E. Santaniello, P. Ciuffreda, ALESSANDRINI, LAURA, A. Repetto, S. Casati
Other Authors: L. Alessandrini
Format: Article in Journal/Newspaper
Language:English
Published: Elsevier Science 2006
Subjects:
lipase
benzoylation
transesterification
alcoholysi
diols
Settore BIO/10 - Biochimica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/23354
https://doi.org/10.1016/j.molcatb.2006.02.014
Description
Summary:Lipases from Mucor miehei (MML) and Candida antarctica (CAL) are able to catalyze the monobenzoylation of the primary hydroxy group of 1,2- 1,4- or 1,5-diols with vinyl benzoate in an organic solvent, the reaction proceeding with high regioselectivity and moderate enantioselectivity. The lipase-catalyzed debenzoylation of 1,2-propanediol dibenzoate by alcoholysis with I-octanol most satisfactorily occurred with Pseudomonas cepacia lipase absorbed onto celite that allowed also to prepare (R)-1-benzoyloxy-2-methylpropan-3-ol from 2-methyl-1,3-propanediol dibenzoate, a result complementary to MML-catalyzed benzoylation of 2-methyl-1,3-propanediol that affords the (S)-monobenzoate.

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