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- 2H)ethanol, prepared via chemoenzymatic syntheses, indicate that the H-atom involved in the 1,2-shift is the pro-S one of the enantiotopic couple of the alcohol function.
Stereochemistry of the conversion of 2-phenoxyethanol into phenol and acetaldehyde by Acetobacterium sp / G. Speranza, B. Mueller, M. Orlandi, C. Morelli, P.M. Manitto, B. Schink. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 86:7(2003), pp. 2629-2636. [10.1002/hlca.200390212]
Stereochemistry of the conversion of 2-phenoxyethanol into phenol and acetaldehyde by Acetobacterium sp
G. SperanzaPrimo
;C. Morelli;P.M. ManittoPenultimo
;
2003
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- 2H)ethanol, prepared via chemoenzymatic syntheses, indicate that the H-atom involved in the 1,2-shift is the pro-S one of the enantiotopic couple of the alcohol function.
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