Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes. (30th November 2018)

• Record Type: Journal Article
• Authors: Demming, Rebecca M.; Hammer, Stephan C.; Nestl, Bettina M.; Gergel, Sebastian; Fademrecht, Silvia; Pleiss, Jürgen; Hauer, Bernhard
• Is Part Of: Angewandte Chemie. Volume 131:Number 1(2019)
• Page Start: 179
• Page End: 183
• Publication Date: 2018-11-30
• Subjects: Alkene -- Asymmetrische Hydratisierung -- Biokatalyse -- Rationales Enzym-Design -- Täuschungsmoleküle; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201810005
• Languages: English
• ISSNs: 0044-8249

Abstract

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.