Stereochemistry of the Conversion of 2??Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp.

…, B Mueller, M Orlandi, CF Morelli, P Manitto…

Index: Speranza, Giovanna; Mueller, Britta; Orlandi, Maximilian; Morelli, Carlo F.; Manitto, Paolo; Schink, Bernhard Helvetica Chimica Acta, 2003 , vol. 86, # 7 p. 2629 - 2636

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Citation Number: 6

Abstract

Abstract The conversion of 2-phenoxyethanol to phenol and acetate by the anaerobic bacterium Acetobacterium sp. strain LuPhet1 proceeds through acetaldehyde with concomitant migration of a H-atom from C (1) to C (2) of the glycolic moiety. Separate feeding experiments with (R)-and (S)-2-phenoxy (1-2 H) ethanol, prepared via chemoenzymatic syntheses, indicate that the H-atom involved in the 1, 2-shift is the pro-S ...