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A stereoselective inverting sec-alkylsulfatase for the deracemization of sec-alcohols.

ABSTRACT: A metallo-?-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.

SUBMITTER: Schober M 

PROVIDER: S-EPMC3155277 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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A stereoselective inverting sec-alkylsulfatase for the deracemization of sec-alcohols.

Schober Markus M   Gadler Petra P   Knaus Tanja T   Kayer Heidemarie H   Birner-Grünberger Ruth R   Gülly Christian C   Macheroux Peter P   Wagner Ulrike U   Faber Kurt K  

Organic letters 20110719 16

A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale. ...[more]

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