Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes.

ABSTRACT: 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.

SUBMITTER: Demming RM 

PROVIDER: S-EPMC6471033 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature