Stereochemistry of the Conversion of 2‐Phenoxyethanol into Phenol and Acetaldehyde by Acetobacterium sp. |
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Authors: | Giovanna Speranza Britta Mueller Maximilian Orlandi CarloF Morelli Paolo Manitto Bernhard Schink |
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Institution: | Giovanna Speranza,Britta Mueller,Maximilian Orlandi,Carlo?F. Morelli,Paolo Manitto,Bernhard Schink |
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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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