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Spectroscopy
Volume 13, Issue 2, Pages 137-143
http://dx.doi.org/10.1155/1997/818060

Catalyzed asymmetric hydrolysis of fluorinated chiral esters in locust haemolymph. In vitro19F NMR monitoring

L. Menguy, S. Hamm, and J. C. Cherton

Laboratoire du SIRCOB, (Structure, Interaction, Réactivité en Chimie Organique et en Bioorganique), EP CNRS 102, Université de Versailles Saint-Quentin en Yvelines, 45 avenue des Etats‒Unis, 78035 Versailles, France

Received 1 July 1996

Copyright © 1997 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

19F NMR is used for monitoring the In vitro behaviour in locust organs or tissues of an ester with a fluorinated alkoxy structure and a chiral acyl moiety. In carrying out analysis directly in the biological media, the problematic extraction of polar metabolites is avoided, contributing to an easier and more reliable monitoring. Thus, in diluted haemolymph a remarkable enantioselectivity of the transformation is evidenced. Over a four hour period the ester R remains unalterated, while the S enantiomer is completely hydrolyzed. This enantioselectivity is the reverse of the trend which is generally observed in the hydrolysis of esters by lipases.