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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes.
- Source :
-
Angewandte Chemie International Edition . Jan2019, Vol. 58 Issue 1, p173-177. 5p. - Publication Year :
- 2019
-
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. Engineered for success: Asymmetric hydration of unactivated, aliphatic alkenes was achieved with a fatty acid hydratase generating chiral alcohols with high conversion, excellent regio‐ and enantioselectivity, and on a preparative scale. Key for high activity is a carboxylic acid decoy molecule that activates the wildtype and engineered enzymes for alkene hydration on alternative substrates. [ABSTRACT FROM AUTHOR]
- Subjects :
- *HYDRATION
*ALKENES
*CHEMICAL alcohol synthesis
*HYDRATASES
*CARBOXYLIC acids
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 58
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 133626577
- Full Text :
- https://doi.org/10.1002/anie.201810005