Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Novel Regioselective Ester Hydrolysis by Pig-Liver Esterase
Amit BasakGautam BhattacharyaSunanda K. Palit
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1997 Volume 70 Issue 10 Pages 2509-2513

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Abstract

Pig-liver esterase, which catalyzed the hydrolysis of substrates containing both saturated and α,β-unsaturated/cyclopropanecarboxylic esters (methyl and ethyl), was studied. An exclusive hydrolysis of the saturated esters was observed. Kinetic experiments revealed that the presence of deactivated carbonyl in the unsaturated/cyclopropanecarboxylic esters and their weaker bindings are both responsible for the observed specificity. The relative binding abilities of the substrates have been explained in light of Jones active-site model. The regioselectivity has been exploited in the synthesis of intermediates for the thromboxane synthetase inhibitor.

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© 1997 The Chemical Society of Japan
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