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Biocatalytic Enantioselective β‐Hydroxylation of Unactivated C−H Bonds in Aliphatic Carboxylic Acids.
- Source :
-
Angewandte Chemie . 7/11/2022, Vol. 134 Issue 28, p1-7. 7p. - Publication Year :
- 2022
-
Abstract
- Catalytic selective hydroxylation of unactivated aliphatic (sp3) C−H bonds without a directing group represents a formidable task for synthetic chemists. Through directed evolution of P450BSβ hydroxylase, we realize oxyfunctionalization of unactivated C−H bonds in a broad spectrum of aliphatic carboxylic acids with varied chain lengths, functional groups and (hetero‐)aromatic moieties in a highly chemo‐, regio‐ and enantioselective fashion (>30 examples, Cβ/Cα>20 : 1, >99 % ee). The X‐ray structure of the evolved variant, P450BSβ‐L78I/Q85H/G290I, in complex with palmitic acid well rationalizes the experimentally observed regio‐ and enantioselectivity, and also reveals a reduced catalytic pocket volume that accounts for the increased reactivity with smaller substrates. This work showcases the potential of employing a biocatalyst to enable a chemical transformation that is particularly challenging by chemical methods. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 134
- Issue :
- 28
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 157801860
- Full Text :
- https://doi.org/10.1002/ange.202204290