Design and Synthesis of Transition State Analogs for Induction of Hydride Transfer Catalytic Antibodies

J Schröer, M Sanner, JL Reymond

Index: Schroeer, Josef; Sanner, Michel; Reymond, Jean-Louis; Lerner, Richard A. Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3220 - 3229

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Citation Number: 12

Abstract

Alcohol dehydrogenases and related aldehyde reductase enzymes catalyze the oxidation of alcohols to aldehydes and the simultaneous reduction of a nicotinamide derivative (NAD+ or NADP+) to the corresponding 1, 4-dihydronicotinamide. Herein we report the design and synthesis of a stable transition state analog for this hydride transfer process. Compound 1 is a rigid [3.2. 2] bicyclic structure containing 3-piperidone oxime as a mimic for 1, 4- ...