The Journal of Organic Chemistry

Distorted amides as models for activated peptide NC: O units produced during enzyme-catalyzed acyl transfer reactions. 1. The mechanism of hydrolysis of 3, 4- …

V Somayaji, RS Brown

Index: Somayaji, V.; Brown, R. S. Journal of Organic Chemistry, 1986 , vol. 51, # 14 p. 2676 - 2686

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Citation Number: 96

Abstract

A series of four substituted benzoquinuclidonea (6-X-3, 4-dihydro-2-oxo-1, 4- ethanoquinolie, X= H, CH3, OCH3, C1)(3a-d) and the next higher homologue [2, 3, 4, 5- tetrahydro-2-oxo-1, 5-ethanobenzazepine (5)] were synthesized and their hydrolyses studied. These are considered as models for the putative distorted amide NC= O unit in the Michaelis complex produced during enzyme-catalyzed hydrolyses of peptides. Compound ...