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Kinetic resolution of (R,S)-2,2-dimethylcyclopropanecarboxamide by Delftia tsuruhatensis ZJB-05174: Role of organic cosolvent in reaction medium

Paper ID Volume ID Publish Year Pages File Format Full-Text
50082 46779 2012 4 PDF Available
Title
Kinetic resolution of (R,S)-2,2-dimethylcyclopropanecarboxamide by Delftia tsuruhatensis ZJB-05174: Role of organic cosolvent in reaction medium
Abstract

Both enantioselectivity and catalytic activity were greatly enhanced in Delftia tsuruhatensis ZJB-05174 catalyzed kinetic resolution of 2,2-dimethlycyclopropanecarboxamide in the presence of ethanol and acetonitrile. The enantiomeric ratio (E) rose from 27 to 140 and 90 by addition of 5% acetonitrile and ethanol, respectively. In the scaled-up biotransformation, the reaction time was shortened to 1.33 h with an ees of 99% and 12.4 g of optically pure product (43.5% total yield) was afforded. These results indicated that addition of cosolvent was a simple and practical tool to improve amidase properties and would be extensively applied in amidase-catalyzed bioprocess.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights►Addition of MeCN enhanced both stereospecificity and activity of amidase. ►Concentration of cosolvent has profound influence on amidase activity and stability. ►Space-time yield of the bioprocess was improved by adding low concentration of MeCN.

Keywords
Amidases; Kinetic resolution; 2,2-Dimethylcyclopropanecarboxamide; Cosolvent; Acetonitrile
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Kinetic resolution of (R,S)-2,2-dimethylcyclopropanecarboxamide by Delftia tsuruhatensis ZJB-05174: Role of organic cosolvent in reaction medium
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 18, 10 February 2012, Pages 68–71
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
Online Support
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