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- Title
Semirational Engineering of the Naphthalene Dioxygenase from <italic>Pseudomonas</italic> sp. NCIB 9816‐4 towards Selective Asymmetric Dihydroxylation.
- Authors
Halder, Julia M.; Nestl, Bettina M.; Hauer, Bernhard
- Abstract
Abstract: Enzyme‐catalyzed asymmetric dihydroxylation is a powerful tool for the selective oxyfunctionalization of various organic compounds. By applying Rieske non‐heme dioxygenases (ROs), molecular oxygen and a reduction equivalent are needed for the generation of vicinal <italic>cis</italic>‐diols. We report a comprehensive mutagenesis study of the active site of the naphthalene dioxygenase from <italic>Pseudomonas</italic> sp. NCIB 9816‐4 comprising 62 variants. We aimed to understand the important structure–function relationships by investigating different substituted arene substrates and the geometry of the active site. Introducing single‐point mutations at positions F202, A206, V260, H295, F352, and L307 resulted in drastic shifts in the reaction specificity, regioselectivity, and stereoselectivity (≥90 %) while maintaining the residual activity towards the natural substrate naphthalene.
- Subjects
NAPHTHALENE; NAPHTHYL compounds; DIOXYGENASES; ENZYMES; MUTAGENESIS; GENETIC mutation
- Publication
ChemCatChem, 2018, Vol 10, Issue 1, p178
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201701262