Stereochemistry of the Conversion of 2-Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp.
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Helvetica Chimica Acta. 2003, 86(7), pp. 2629-2636. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/hlca.200390212
Zusammenfassung
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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570 Biowissenschaften, Biologie
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SPERANZA, Giovanna, Britta MÃœLLER, Maximilian ORLANDI, Carlo F. MORELLI, Paolo MANITTO, Bernhard SCHINK, 2003. Stereochemistry of the Conversion of 2-Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp.. In: Helvetica Chimica Acta. 2003, 86(7), pp. 2629-2636. ISSN 0018-019X. eISSN 1522-2675. Available under: doi: 10.1002/hlca.200390212BibTex
@article{Speranza2003Stere-7648, year={2003}, doi={10.1002/hlca.200390212}, title={Stereochemistry of the Conversion of 2-Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp.}, number={7}, volume={86}, issn={0018-019X}, journal={Helvetica Chimica Acta}, pages={2629--2636}, author={Speranza, Giovanna and Müller, Britta and Orlandi, Maximilian and Morelli, Carlo F. and Manitto, Paolo and Schink, Bernhard} }
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