{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,20]],"date-time":"2026-07-20T15:46:19Z","timestamp":1784562379192,"version":"3.55.0"},"reference-count":39,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2021,7,8]],"date-time":"2021-07-08T00:00:00Z","timestamp":1625702400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2021,9]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>There is a considerable interest in the asymmetric production of chiral allylic alcohols, the main building blocks of many functional molecules. The asymmetric reduction of \u03b1,\u03b2\u2010unsaturated ketones is difficult with traditional chemical protocols in a regioselective and stereoselective manner. In this study, the reductive capacity of whole cell of <jats:italic>Leuconostoc mesenteroides<\/jats:italic> N6, <jats:italic>Weissella paramesenteroides<\/jats:italic> N7, <jats:italic>Weissella cibaria<\/jats:italic> N9, and <jats:italic>Leuconostoc pseudomesenteroides<\/jats:italic> N13 was investigated as whole\u2010cell biocatalysts in the enantioselective reduction of (<jats:italic>E<\/jats:italic>)\u20104\u2010phenylbut\u20103\u2010en\u20102\u2010one (<jats:bold>1<\/jats:bold>). The biocatalytic reduction of <jats:bold>1<\/jats:bold> to (<jats:italic>S<\/jats:italic>,<jats:italic>E<\/jats:italic>)\u20104\u2010phenylbut\u20103\u2010en\u20102\u2010ol (<jats:bold>(<jats:italic>S<\/jats:italic>,<jats:italic>E<\/jats:italic>)\u20102<\/jats:bold>) using the whole cell of <jats:italic>W<\/jats:italic>.\u00a0<jats:italic>cibaria<\/jats:italic> N9 isolated from Turkish sourdough was developed in a regioselective fashion, occurring with excellent conversion and recovering the product in good yield. In biocatalytic reduction reactions, the conversion of the substrate and the enantiomeric excess (ee) of the product are significantly affected by optimization parameters such as temperature, agitation rate, pH, and incubation time. Effects of these parameters on ee and conversion were investigated comprehensively. In addition, to our knowledge, this is the first report on production of <jats:bold>(<jats:italic>S<\/jats:italic>,<jats:italic>E<\/jats:italic>)\u20102<\/jats:bold> using whole\u2010cell biocatalyst in excellent yield, conversion with enantiopure form and at gram scale. These findings pave the way for the use of whole cell of <jats:italic>W<\/jats:italic>.\u00a0<jats:italic>cibaria<\/jats:italic> N9 for challenging higher substrate concentrations of different \u03b1,\u03b2\u2010unsaturated ketones for regioselective reduction at industrial scale.<\/jats:p>","DOI":"10.1002\/chir.23337","type":"journal-article","created":{"date-parts":[[2021,7,9]],"date-time":"2021-07-09T04:01:04Z","timestamp":1625803264000},"page":"535-542","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Regioselective asymmetric bioreduction of <i>trans<\/i>\u20104\u2010phenylbut\u20103\u2010en\u20102\u2010one by whole\u2010cell of <i>Weissella cibaria<\/i> N9 biocatalyst"],"prefix":"10.1002","volume":"33","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4656-8254","authenticated-orcid":false,"given":"Erbay","family":"Kalay","sequence":"first","affiliation":[{"name":"Kars Vocational School Kafkas University  Kars Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3723-1705","authenticated-orcid":false,"given":"Engin","family":"\u015eahin","sequence":"additional","affiliation":[{"name":"Faculty of Health Sciences, Department of Nutrition and Dietetics Bayburt University  Bayburt Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,7,8]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300599"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204579"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03546"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03709"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000204)39:3<569::AID-ANIE569>3.0.CO;2-8"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/b303250g"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/b512139f"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200328h"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02591"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.10.051"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01952"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201908012"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/C2CS35333D"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0167-7799(02)01935-2"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2007.10.031"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198806221"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3gc41457d"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2012.09.014"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201900921"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2011.11.014"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00950"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cogsc.2018.03.015"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201610990"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.lwt.2016.03.030"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23048"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201700269"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcatb.2011.02.011"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA00883C"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2020.1729809"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.23123"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.procbio.2005.06.028"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1872-2067(08)60103-5"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1004-9541(11)60087-6"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1080\/10242422.2017.1420063"},{"key":"e_1_2_6_36_1","first-page":"297","article-title":"Development and validation of a kinetic model for enzymatic hydrolysis using Candida rugosa lipase","volume":"7","author":"Jamie A","year":"2017","journal-title":"J Bioprocess Biotech"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/jctb.1392"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2016.01.008"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2010.03.005"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2013.09.041"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.23337","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chir.23337","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.23337","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,29]],"date-time":"2023-08-29T21:47:33Z","timestamp":1693345653000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.23337"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,7,8]]},"references-count":39,"journal-issue":{"issue":"9","published-print":{"date-parts":[[2021,9]]}},"alternative-id":["10.1002\/chir.23337"],"URL":"https:\/\/doi.org\/10.1002\/chir.23337","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"value":"0899-0042","type":"print"},{"value":"1520-636X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,7,8]]},"assertion":[{"value":"2021-03-22","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-06-24","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-07-08","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}