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Vol. 26 No. 2 (2014): Vol 26 Issue 2

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Novozyme 435 Asymmetric Hydrolysis of Enol Ester with Series Acid Moiety

https://doi.org/10.14233/ajchem.2014.16200
Quan Li
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P.R. China *Corresponding author: Tel: +86 13817705124; E-mail: sying5@126.com
Weimin Jia*
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P.R. China *Corresponding author: Tel: +86 13817705124; E-mail: sying5@126.com
Zhijian Wang
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P.R. China *Corresponding author: Tel: +86 13817705124; E-mail: sying5@126.com
Xiaodan Guo
School of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai, P.R. China *Corresponding author: Tel: +86 13817705124; E-mail: sying5@126.com

Asian Journal of Chemistry, Vol. 26 No. 2 (2014): Vol 26 Issue 2

Abstract

(R)-2-pentylcyclopentanone can be synthesized by the asymmetric hydrolysis of enol esters, catalyzed by immobilized candida antarctica (novozyme 435) lipase. Different acid moieties influence the stereoselectivity of lipase. Enol esters can be prepared from anhydrides and 2-pentylcyclopentanone. When introducing optical (S)-(+)-2-methyl-butyric acid, the hydrolysis of optical enol ester showed great enhancement of the specific rotation compared to the racemic enol ester, the specific rotation of product raise from [a]25D-10° (c 0.1, CH3OH) to [a]25D-72° (c 0.1, CH3OH). However, when bringing chiral acid moity, the specific rotation still can not catch up with the value compared to the isobutyric moiety. The specific rotation of (R)-2-pentylcyclopentanone is [a]25D-102.20° (c 0.1, CH3OH), the optimum temperature and pH were 30 °C and 6.5, respectively. Then 81.06 % ee of (R)-d-decalactone was prepared by the Baeyer-Villiger oxidation of (R)-2-pentylcyclopentanone.

Keywords

Asymmetric hydrolysis Specific rotation Enol ester (R)-2-Pentylcyclopentanone Chiral acid moiety.
Li, Q., Jia*, W., Wang, Z., & Guo, X. (2014). Novozyme 435 Asymmetric Hydrolysis of Enol Ester with Series Acid Moiety. Asian Journal of Chemistry, 26(2), 607–610. https://doi.org/10.14233/ajchem.2014.16200
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