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Regiospecific Ester Hydrolysis by Orange Peel Esterase - An Undergraduate Experiment.

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Timothy D.H. Bugg , Andrew M. Lewin and Eric R. Catlin

Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.

J. Chem. Educ., 1997, 74 (1), p 105

DOI: 10.1021/ed074p105

Publication Date (Web): January 1, 1997

Section:

History, Education, and Documentation

Abstract

A simple but effective experiment has been developed to demonstrate the regiospecificity of enzyme catalysis using an esterase activity easily isolated from orange peel. The experiment involves the preparation of diester derivatives of para-, meta- and ortho-hydroxybenzoic acid (e.g. methyl 4-acetoxy-benzoic acid). The derivatives are incubated with orange peel esterase, as a crude extract, and with commercially available pig liver esterase and porcine pancreatic lipase. The enzymatic hydrolysis reactions are monitored by thin layer chromatography, revealing which of the two ester groups is hydrolysed, and the rate of the enzyme-catalysed reaction.

The results of a group experiment revealed that in all cases hydrolysis was observed with at least one enzyme, and in most cases the enzymatic hydrolysis was specific for production of either the hydroxy-ester or acyl-acid product. Specificity towards the ortho-substituted series was markedly different to that of the para-substituted series, which could be rationalised in the case of pig liver esterase by a published active site model.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Esters

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