Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica

• Published in: Molecules
• Main Authors: Hercules V. Ferreira, Lenilson C. Rocha, Richele P. Severino, André L. M. Porto
• Format: Text
• Language: English
• Published: Molecular Diversity Preservation International 2012
• Subjects: kinetic resolution; lipase; Candida antarctica; aliphatic secondary alcohols; Antarc*; Antarctica
• Online Access: https://doi.org/10.3390/molecules17088955

The lipase B from Candida antarctica (Novozym 435®, CALB) efficiently catalyzed the kinetic resolution of some aliphatic secondary alcohols: (±)-4-methylpentan-2-ol (1), (±)-5-methylhexan-2-ol (3), (±)-octan-2-ol (4), (±)-heptan-3-ol (5) and (±)-oct-1-en-3-ol (6). The lipase showed excellent enantioselectivities in the transesterifications of racemic aliphatic secondary alcohols producing the enantiopure alcohols (>99% ee) and acetates (>99% ee) with good yields. Kinetic resolution of rac-alcohols was successfully achieved with CALB lipase using simple conditions, vinyl acetate as acylating agent, and hexane as non-polar solvent.