3 years ago

Kinetic Resolution of sec-Thiols via Enantioselective Oxidation with Rationally Engineered 5-(Hydroxymethyl)furfural Oxidase

Claudia Binda, Elvira Romero, Alexander Swoboda, Marco Fraaije, Andrea Mattevi, Christoph Winkler, Kurt Faber, Mathias Pickl
Various flavoprotein oxidases were recently shown to oxidize prim-thiols. Here we extend this reactivity towards sec-thiols via structure-guided engineering of 5-(hydroxymethyl)furfural oxidase (HMFO). The variants obtained were employed for the oxidative kinetic resolution of rac-sec-thiols yielding the correspon¬ding thioketones and nonreacted (R)-thiols with excellent enantioselectivities (E ≥ 200). The engineering strategy applied went beyond the classic approach of replacing bulky amino acid residues with smaller ones, as the active site was additionally enlarged by a newly introduced Thr residue that establishes a hydrogen bonding interaction with the substrates, as predicted by modelling and verified in the crystal structure of the variant. These strategies unlocked HMFO variants for the enantioselective oxidation of a range of sec-thiols.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201713189

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