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Carica papaya lipase: An effective biocatalyst for esterification resolution of (RS)-2-(chlorophenoxy)propionic acid

Paper ID Volume ID Publish Year Pages File Format Full-Text
4706 239 2007 7 PDF Available
Title
Carica papaya lipase: An effective biocatalyst for esterification resolution of (RS)-2-(chlorophenoxy)propionic acid
Abstract

A partially purified Carica papaya (pCPL) is explored as an effective biocatalyst for the esterification resolution of (RS)-2-(chlorophenoxy)propionic acid (CPA) with trimethylsilylmethanol in anhydrous isooctane. In comparison with a crude Candida rugosa lipase (CRL), pCPL has higher enantioselectivity (E > 100) for 2- and 4-chloro but not 3-chloro substituted CPA, in which more than an order-of-magnitude lower reactivity for the hindered (RS)-2-(2-chlorophenoxy)propionic acid is found for both lipases. The thermodynamic analysis indicates that the enantiomeric discrimination is mainly driven by the difference of activation enthalpy (ΔΔH) in the present reaction conditions. A linear enthalpy-entropy compensation effect between ΔΔH and the difference of activation entropy (ΔΔS) is demonstrated and elucidated from the regio-effect of 2-, 3- and 4-chloro substituent. The kinetic analysis indicates that pCPL is strongly inhibited by the acid substrate, but to a less extent by the alcohol substrate. With the disadvantage of decreasing the enzyme activity, the E value can be greatly enhanced when trimethylsilylmethanol concentration higher than 40 mM in isooctane is employed.

Keywords
Carica papaya lipase; Esterification; (R,S)-2-(Chlorophenoxy)propionic acid; Regio-substituent effect
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Carica papaya lipase: An effective biocatalyst for esterification resolution of (RS)-2-(chlorophenoxy)propionic acid
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Publisher
Database: Elsevier - ScienceDirect
Journal: Biochemical Engineering Journal - Volume 35, Issue 3, 1 August 2007, Pages 318–324
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us