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Issue 12, 2003
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Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

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Abstract

13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.

Graphical abstract: Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

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Article information


Submitted
05 Mar 2003
Accepted
12 May 2003
First published
27 May 2003

Org. Biomol. Chem., 2003,1, 2103-2110
Article type
Paper

Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: synthesis and mechanism of action

D. C. Martyn, A. J. Vernall, B. M. Clark and A. D. Abell, Org. Biomol. Chem., 2003, 1, 2103
DOI: 10.1039/B302411C

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