Quantitative Improvements and Insights into CALB‐Catalyzed Resolution of trans‐ and cis‐2‐Phenylcyclopropyl Azolides

Abstract With trans ‐2‐phenylcyclopropyl azolides as the model substrate for hydrolytic or alcoholic resolution in methyl tert ‐butyl ether (MTBE) via Novozym 435 as an immobilized Candida antarctica lipase B (CALB), quantitative improvements of the enzyme activity and enantioselectivity were report...

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Bibliographic Details
Published in:ChemistrySelect
Main Authors: Yeh, Yan‐Ru, Tzeng, Yi‐Jia, Tsai, Shau‐Wei
Other Authors: Ministry of Science and Technology
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2018
Subjects:
Antarc*
Antarctica
Online Access:http://dx.doi.org/10.1002/slct.201800578
https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fslct.201800578
https://onlinelibrary.wiley.com/doi/pdf/10.1002/slct.201800578
https://onlinelibrary.wiley.com/doi/full-xml/10.1002/slct.201800578
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Summary:Abstract With trans ‐2‐phenylcyclopropyl azolides as the model substrate for hydrolytic or alcoholic resolution in methyl tert ‐butyl ether (MTBE) via Novozym 435 as an immobilized Candida antarctica lipase B (CALB), quantitative improvements of the enzyme activity and enantioselectivity were reported. At the best reaction conditions of 35 o C, leading to k 2RR K mRR −1 =5.185 L/h⋅g and E trans =97.2, for hydrolysis of trans ‐2‐phenylcyclopropyl 1,2,4‐azolide ( trans ‐2‐PCPT), (1R,2R)‐2‐PCPCA of high optical purity was obtained. Insights into CALB performance via kinetic and thermodynamic analysis for trans ‐ and cis ‐2‐phenylcyclopropyl 1,2,4‐triazolide ( cis ‐2‐PCPT) were furthermore addressed, showing the prospect of present kinetic resolution process for synthesizing other optically pure 2‐arylcyclopropane‐1‐carboxylic acids.

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