Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes | Zendy

Demming Rebecca M. | Zendy; Hammer Stephan C. | Zendy; Nestl Bettina M. | Zendy; Gergel Sebastian | Zendy; Fademrecht Silvia | Zendy; Pleiss Jürgen | Zendy; Hauer Bernhard | Zendy

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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Author(s) -

Demming Rebecca M.,

Hammer Stephan C.,

Nestl Bettina M.,

Gergel Sebastian,

Fademrecht Silvia,

Pleiss Jürgen,

Hauer Bernhard

Publication year - 2019

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201810005

Subject(s) - chemistry , enantioselective synthesis , regioselectivity , catalysis , selectivity , enzyme , organic chemistry , enzyme catalysis , biocatalysis , alkene , carboxylic acid , combinatorial chemistry , reaction mechanism

The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica , asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee , >95 % regioselectivity), and on a preparative scale.

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