A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols

[Image: see text] 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 nonrea...

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Detalles Bibliográficos
Autores principales: Schober, Markus, Gadler, Petra, Knaus, Tanja, Kayer, Heidemarie, Birner-Grünberger, Ruth, Gülly, Christian, Macheroux, Peter, Wagner, Ulrike, Faber, Kurt
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2011
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155277/
https://www.ncbi.nlm.nih.gov/pubmed/21770430
http://dx.doi.org/10.1021/ol201635y
Descripción
Sumario:[Image: see text] 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.

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