4217-66-7 Semirational Engineering of the Naphthalene Dioxygenase from Pseudomonas sp. NCIB 9816-4 towards Selective Asymmetric Dihydroxylation

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 cis-diols. We report a comprehensive mutagenesis study of the active site of the naphthalene dioxygenase from Pseudomonas 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. https://www.lookchem.com/CASDataBase_4217-66-7.htm

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