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The regioselectivity of BVMOs is essential for determining the ratio of the two regioisomeric products (\u201cnormal\u201d and \u201cabnormal\u201d) when catalyzing asymmetric ketone substrates. Starting from a known normal\u2010preferring BVMO sequence from <jats:italic>Pseudomonas putida<\/jats:italic> KT2440 (<jats:italic>Pp<\/jats:italic>BVMO), a novel BVMO from <jats:italic>Gordonia sihwensis<\/jats:italic> (<jats:italic>Gs<\/jats:italic>BVMO) with higher normal regioselectivity (up to 97\/3) was identified. Furthermore, protein engineering increased the specificity constant (<jats:italic>k<\/jats:italic><jats:sub>cat<\/jats:sub>\/<jats:italic>K<\/jats:italic><jats:sub>M<\/jats:sub>) 8.9\u2010fold to 484\u2005s<jats:sup>\u22121<\/jats:sup>\u2009mM<jats:sup>\u22121<\/jats:sup> for 10\u2010ketostearic acid derived from oleic acid. Consequently, by using the variant <jats:italic>Gs<\/jats:italic>BVMO<jats:sub>C308L<\/jats:sub> as an efficient biocatalyst, 10\u2010ketostearic acid was efficiently transformed into 9\u2010(nonanoyloxy)nonanoic acid, with a space\u2010time yield of 60.5\u2005g\u2009L<jats:sup>\u22121<\/jats:sup>\u2009d<jats:sup>\u22121<\/jats:sup>. This study showed that the mutant with higher regioselectivity and catalytic efficiency could be applied to prepare medium\u2010chain \u03c9\u2010hydroxy fatty acids through biotransformation of long\u2010chain aliphatic keto acids derived from renewable plant oils.<\/jats:p>","DOI":"10.1002\/cbic.202000478","type":"journal-article","created":{"date-parts":[[2020,11,18]],"date-time":"2020-11-18T02:01:32Z","timestamp":1605664892000},"page":"1190-1195","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Discovery and Engineering of a Novel Baeyer\u2010Villiger Monooxygenase with High Normal Regioselectivity"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1675-9858","authenticated-orcid":false,"given":"Guang\u2010Xiang","family":"Zhang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Bioreactor Engineering Shanghai Collaborative Innovation Center for Biomanufacturing East China University of Science and Technology  Shanghai 200237 P. R. China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5420-1842","authenticated-orcid":false,"given":"Zhi\u2010Neng","family":"You","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioreactor Engineering Shanghai Collaborative Innovation Center for Biomanufacturing East China University of Science and Technology  Shanghai 200237 P. R. China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jia\u2010Mei","family":"Yu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioreactor Engineering Shanghai Collaborative Innovation Center for Biomanufacturing East China University of Science and Technology  Shanghai 200237 P. R. 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