Direct O-acylation of small molecules containing CO2----HN. rarw. HO units by a distorted amide: enhancement of amine basicity by a pendant carboxylate in a serine …

KI Skorey, V Somayaji, RS Brown

Index: Skorey, K. I.; Somayaji, V.; Brown, R. S. Journal of the American Chemical Society, 1989 , vol. 111, # 4 p. 1445 - 1452

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Citation Number: 26

Abstract

Abstract: The kinetics of the reaction of two series of amino alcohols (ethanol amines and 2- hydroxymethylimidazoles) with a distorted amide were studied as models for the acylation of the serine proteases. The pH/log kZmax profiles plateau above the amine pKa, indicating the basic form is active. In all cases, the reactions proceed by initial 0-acylation to produce esters. With primary or secondary ethanolamines, subsequent 0-N acyl transfer occurs to ...