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

Molecules

Hercules V. Ferreira¹  Lenilson C. Rocha¹  Richele P. Severino¹ 

[1] Institute of Chemistry of São Carlos, University of São Paulo, Av. Trabalhador São-carlense, 400, 13560-970, São Carlos, SP, Brazil;

关键词: kinetic resolution;    lipase;    Candida antarctica;    aliphatic secondary alcohols;   

DOI  :  10.3390/molecules17088955

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.