syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase b from candida antarctica合成的enantiopure脂肪族二醇,醋酸纤维素bioresolution从南极假丝酵母脂肪酶b.pdfVIP

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syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase b from candida antarctica合成的enantiopure脂肪族二醇,醋酸纤维素bioresolution从南极假丝酵母脂肪酶b.pdf

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syntheses of enantiopure aliphatic secondary alcohols and acetates by bioresolution with lipase b from candida antarctica合成的enantiopure脂肪族二醇,醋酸纤维素bioresolution从南极假丝酵母脂肪酶b

Molecules 2012, 17, 8955-8967; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Syntheses of Enantiopure Aliphatic Secondary Alcohols and Acetates by Bioresolution with Lipase B from Candida antarctica Hercules V. Ferreira 1, Lenilson C. Rocha 1, Richele P. Severino 1,2 and André L. M. Porto 1,* 1 Institute of Chemistry of São Carlos, University of São Paulo, Av. Trabalhador São-carlense, 400, 13560-970, São Carlos, SP, Brazil; E-Mails: hercules_quimica@ (H.V.F.); lenilson@iqsc.usp.br (L.C.R.); richeleps@.br (R.P.S.) 2 Department of Chemistry, Federal University of Goias, Campus Advanced of Catalão, Av. Dr. Lamartine Pinto de Avelar, 1120, 75704-020, Catalão, GO, Brazil * Author to whom correspondence should be addressed; E-Mail: almporto@iqsc.usp.br; Tel.: +55-16-3373-8103; Fax: +55-16-3372-9952. Received: 24 April 2012; in revised form: 27 June 2012 / Accepted: 3 July 2012 / Published: 26 July 2012 Abstract: 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 lip