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Substrates, in which the carboxylate group of the benzoic acid moiety is replaced were oxidised with high activity by the S244D mutant (product formation rates &gt;60\u2005nmol.(nmol\u2010CYP)<jats:sup>\u22121<\/jats:sup>.min<jats:sup>\u22121<\/jats:sup>) and with total turnover numbers of up to 20,000. Ethyl \u03b1\u2010hydroxylation was more rapid than methyl oxidation, styrene epoxidation and <jats:italic>S<\/jats:italic>\u2010oxidation. The S244D mutant catalysed the ethyl hydroxylation, epoxidation and sulfoxidation reactions with an excess of one stereoisomer (in some instances up to &gt;98\u2009%). The crystal structure of 4\u2010methoxybenzoic acid\u2010bound CYP199A4 S244D showed that the active site architecture and the substrate orientation were similar to that of the WT enzyme. Overall, this work demonstrates that CYP199A4 can catalyse the stereoselective hydroxylation, epoxidation or sulfoxidation of substituted benzene substrates under mild conditions resulting in more sustainable transformations using this heme monooxygenase enzyme.<\/jats:p>","DOI":"10.1002\/chem.202102757","type":"journal-article","created":{"date-parts":[[2021,8,4]],"date-time":"2021-08-04T22:00:07Z","timestamp":1628114407000},"page":"14765-14777","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["The Stereoselective Oxidation of <i>para<\/i>\u2010Substituted Benzenes by a Cytochrome P450 Biocatalyst"],"prefix":"10.1002","volume":"27","author":[{"given":"Rebecca R.","family":"Chao","sequence":"first","affiliation":[{"name":"Department of Chemistry University Adelaide  Adelaide SA 5005 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ian C.\u2010K.","family":"Lau","sequence":"additional","affiliation":[{"name":"Department of Chemistry University Adelaide  Adelaide SA 5005 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tom","family":"Coleman","sequence":"additional","affiliation":[{"name":"Department of Chemistry University Adelaide  Adelaide SA 5005 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Luke R.","family":"Churchman","sequence":"additional","affiliation":[{"name":"School of Chemistry and Molecular Bioscience University of Queensland  Brisbane Qld 4072 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stella A.","family":"Child","sequence":"additional","affiliation":[{"name":"Department of Chemistry University Adelaide  Adelaide SA 5005 Australia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joel H. 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