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

• 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

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.