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Among these, group E monooxygenases (GEMs) catalyze enantioselective epoxidation and sulfoxidation reactions. Here, we describe the crystal structure of an indole monooxygenase from the bacterium <jats:italic>Variovorax paradoxus<\/jats:italic> EPS, a GEM designated as <jats:italic>Vp<\/jats:italic>IndA1. Complex structures with substrates reveal productive binding modes that, in conjunction with force\u2010field calculations and rapid mixing kinetics, reveal the structural basis of substrate and stereoselectivity. Structure\u2010based redesign of the substrate cavity yielded variants with new substrate selectivity (for sulfoxidation of benzyl phenyl sulfide) or with greatly enhanced stereoselectivity (from 35.1\u2009% to 99.8\u2009% <jats:italic>ee<\/jats:italic> for production of (1<jats:italic>S<\/jats:italic>,2<jats:italic>R<\/jats:italic>)\u2010indene oxide). This first determination of the substrate binding mode of GEMs combined with structure\u2010function relationships opens the door for structure\u2010based design of these powerful biocatalysts.<\/jats:p>","DOI":"10.1002\/anie.202300657","type":"journal-article","created":{"date-parts":[[2023,2,10]],"date-time":"2023-02-10T14:49:25Z","timestamp":1676040565000},"update-policy":"http:\/\/dx.doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Structural and Mechanistic Studies on Substrate and Stereoselectivity of the Indole Monooxygenase <i>Vp<\/i>IndA1: New Avenues for Biocatalytic Epoxidations and Sulfoxidations"],"prefix":"10.1002","volume":"62","author":[{"ORCID":"http:\/\/orcid.org\/0000-0001-8597-4856","authenticated-orcid":false,"given":"Julia","family":"Kratky","sequence":"first","affiliation":[{"name":"Institute of Bioanalytical Chemistry Leipzig University Deutscher Platz\u20055 04103 Leipzig 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