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To gain insight into the molecular basis of enzyme stereo\u2010recognition and expand the source of antiPrelog carbonyl reductase toward \u03b2\u2010ketoesters, rational enzyme design aiming at stereoselectivity inversion was performed. The designed variant Q139G switched the enzyme stereoselectivity toward \u03b2\u2010ketoesters from Prelog to antiPrelog, providing corresponding alcohols in high enantiomeric purity (89.1\u201399.1\u2009% <jats:italic>ee<\/jats:italic>). More importantly, the well\u2010known trade\u2010off between stereoselectivity and activity was not found. Q139G exhibited higher catalytic activity than the wildtype enzyme, the enhancement of the catalytic efficiency (<jats:italic>k<\/jats:italic><jats:sub>cat<\/jats:sub>\/<jats:italic>K<\/jats:italic><jats:sub>m<\/jats:sub>) varied from 1.1\u2010 to 27.1\u2010fold. Interestingly, the mutant Q139G did not lead to reversed stereoselectivity toward aromatic ketones. Analysis of enzyme\u2013substrate complexes showed that the structural flexibility of \u03b2\u2010ketoesters and a newly formed cave together facilitated the formation of the antiPrelog\u2010preferred conformation. In contrast, the relatively large and rigid structure of the aromatic ketones prevents them from forming the antiPrelog\u2010preferred conformation.<\/jats:p>","DOI":"10.1002\/chem.202005195","type":"journal-article","created":{"date-parts":[[2021,1,21]],"date-time":"2021-01-21T13:19:25Z","timestamp":1611235165000},"page":"6283-6294","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Single\u2010Point Mutant Inverts the Stereoselectivity of a Carbonyl Reductase toward \u03b2\u2010Ketoesters with Enhanced Activity"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5582-0493","authenticated-orcid":false,"given":"Aipeng","family":"Li","sequence":"first","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"},{"name":"Research &amp; Development Institute in Shenzhen Northwestern Polytechnical University  518057 Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"},{"name":"Research &amp; Development Institute in Shenzhen Northwestern Polytechnical University  518057 Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qing","family":"Tian","sequence":"additional","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"},{"name":"Research &amp; Development Institute in Shenzhen Northwestern Polytechnical University  518057 Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaohong","family":"Yang","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of California  One Shields Avenue Davis California 95616 United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dongming","family":"Yin","sequence":"additional","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"},{"name":"Research &amp; Development Institute in Shenzhen Northwestern Polytechnical University  518057 Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5567-1464","authenticated-orcid":false,"given":"Yong","family":"Qin","sequence":"additional","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7803-6028","authenticated-orcid":false,"given":"Lianbing","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Life Sciences Northwestern Polytechnical University  710072 Xi'an China"},{"name":"Research &amp; Development Institute in Shenzhen Northwestern Polytechnical University  518057 Shenzhen China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,3,7]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00950"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CY02409F"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020617)41:12<2008::AID-ANIE2008>3.0.CO;2-4"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020617)114:12<2108::AID-ANGE2108>3.0.CO;2-Z"},{"key":"e_1_2_7_5_1","unstructured":"\u00a0"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.201900413"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.procbio.2018.12.011"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-017-02698-4"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41929-017-0010-4"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.biortech.2017.09.204"},{"key":"e_1_2_7_12_2","author":"Han M.","year":"2020","journal-title":"Microb. 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