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Enantioselective Esterification Of (±)-Menthol With Butyric Anhydride By Chemically Modified Candida Rugosa Lipase


Citation

Jasmani, Halila (2003) Enantioselective Esterification Of (±)-Menthol With Butyric Anhydride By Chemically Modified Candida Rugosa Lipase. PhD thesis, Universiti Putra Malaysia.

Abstract / Synopsis

Commercial lipase from Candida rugosa was chemically modified with the aim to improve its catalytic properties in organic solvents. The chemical modifiers, aldehydes and monomethoxy polyethylene glycols, were covalently linked to the lysine residues at the surface of the enzyme. Enzymatic enantioselective esterification of racemic menthol in organic solvents using butyric anhydride as acylating agent was performed with the chemically modified lipases. Different degrees of modification, organic solvents, reaction temperatures and water activity were examined for the influence on the percent yield and enantioselective formation of (-)-menthyl butyrate. The percent yield increased as the degree of modification increased but decreased slightly for the highest degree of modification. Organic solvents with log P values above 2.5 gave higher yield, however high enantioselectivity was obtained in all the organic solvents tested. The enantioselectivity towards (-)-menthol decreased considerably as the reaction temperature was increased. Enzyme derivatives exhibited better activity and enantioselectivity at high aw. The alkylated lipases showed higher thermal, solvent


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Additional Metadata

Item Type: Thesis (PhD)
Subject: Enantioselective catalysis
Subject: Lipase
Subject: Esterification
Call Number: FSAS 2003 18
Chairman Supervisor: Professor Abu Bakar Salleh, PhD
Divisions: Faculty of Environmental Studies
Depositing User: Mohd Nezeri Mohamad
Date Deposited: 22 Jul 2011 01:03
Last Modified: 19 Dec 2012 06:47
URI: http://psasir.upm.edu.my/id/eprint/11622
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