{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,29]],"date-time":"2026-05-29T21:12:03Z","timestamp":1780089123477,"version":"3.54.0"},"reference-count":51,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2025,3,27]],"date-time":"2025-03-27T00:00:00Z","timestamp":1743033600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["17H06169"],"award-info":[{"award-number":["17H06169"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["22H00361"],"award-info":[{"award-number":["22H00361"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2025,6,3]]},"abstract":"<jats:p>\n                    Chiral 3,3,3\u2010trifluoro\u20102\u2010hydroxypropanoic acid (3,3,3\u2010trifluorolactic acid, TFLA), which possesses two significant functional groups, is a versatile intermediate in pharmaceutical and material synthesis. A feasible strategy for producing both the enantiomers of chiral TFLAs involves reduction of the corresponding pyruvate using lactate dehydrogenases (LDHs). In this study,\n                    <jats:italic>ldh<\/jats:italic>\n                    genes encoding\n                    <jats:sc>l<\/jats:sc>\n                    \u2010LDHs from animals and\n                    <jats:sc>d<\/jats:sc>\n                    \/\n                    <jats:sc>l<\/jats:sc>\n                    \u2010LDHs from lactic acid bacteria are cloned and all the recombinant LDHs are successfully expressed with a histidine tag in\n                    <jats:italic>Escherichia coli<\/jats:italic>\n                    BL21 (DE3). To achieve cofactor regeneration, a nicotinamide adenine dinucleotide regeneration system is constructed using formate dehydrogenase from\n                    <jats:italic>Candida boidinii<\/jats:italic>\n                    . Chiral TFLA is synthesized from 3,3,3\u2010trifluoro\u20102\u2010oxopropionic acid (trifluoropyruvic acid, TFPy) with good yields and excellent stereoselectivity, catalyzed by lactate dehydrogenases and formate dehydrogenase. Under optimized biocatalytic conditions, highly active\n                    <jats:sc>d<\/jats:sc>\n                    \u2010\n                    <jats:italic>Lm<\/jats:italic>\n                    LDH from\n                    <jats:italic>Leuconostoc mesenteroides<\/jats:italic>\n                    and chicken\n                    <jats:sc>l<\/jats:sc>\n                    \u2010LDH from\n                    <jats:italic>Gallus<\/jats:italic>\n                    are screened for their ability to completely convert 0.5\u2009\n                    <jats:sc>m<\/jats:sc>\n                    TFPy to produce optically pure (\n                    <jats:italic>S<\/jats:italic>\n                    )\u2010TFLA and (\n                    <jats:italic>R<\/jats:italic>\n                    )\u2010TFLA with enantiomeric excess &gt;99.5% within 6\u2009h, respectively. Molecular docking simulations investigate the catalytic mechanisms of selected\n                    <jats:sc>d<\/jats:sc>\n                    \u2010LDH and\n                    <jats:sc>l<\/jats:sc>\n                    \u2010LDH, revealing their activity and stereoselectivity toward \uf8ffCF\n                    <jats:sub>3<\/jats:sub>\n                    \u2010containing TFPy.\n                  <\/jats:p>","DOI":"10.1002\/cbic.202500047","type":"journal-article","created":{"date-parts":[[2025,3,30]],"date-time":"2025-03-30T07:00:10Z","timestamp":1743318010000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Study on the Asymmetric Synthesis of Chiral 3,3,3\u2010Trifluoro\u20102\u2010Hydroxypropanoic Acids by Lactate Dehydrogenase"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0009-0003-2579-6826","authenticated-orcid":false,"given":"Jingfei","family":"Wu","sequence":"first","affiliation":[{"name":"Biotechnology Research Center and Department of Biotechnology Toyama Prefectural University  5180 Kurokawa, Imizu Toyama 939\u20100398 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8312-9592","authenticated-orcid":false,"given":"Aem","family":"Nuylert","sequence":"additional","affiliation":[{"name":"Biotechnology Research Center and Department of Biotechnology Toyama Prefectural University  5180 Kurokawa, Imizu Toyama 939\u20100398 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Misako","family":"Iwaki","sequence":"additional","affiliation":[{"name":"Biotechnology Research Center and Department of Biotechnology Toyama Prefectural University  5180 Kurokawa, Imizu Toyama 939\u20100398 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shinsuke","family":"Miki","sequence":"additional","affiliation":[{"name":"New\u2010STEP Research Center Central Glass Co., Ltd.  17\u20105, Nakadai 2\u2010chome Kawagoe City Saitama 350\u20101159 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3645-3952","authenticated-orcid":false,"given":"Yasuhisa","family":"Asano","sequence":"additional","affiliation":[{"name":"Biotechnology Research Center and Department of Biotechnology Toyama Prefectural University  5180 Kurokawa, Imizu Toyama 939\u20100398 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,3,27]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"crossref","first-page":"10633","DOI":"10.1021\/acsomega.0c00830","volume":"5","author":"Inoue M.","year":"2020","journal-title":"ACS Omega"},{"key":"e_1_2_7_3_1","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.jfluchem.2014.06.026","volume":"167","author":"Zhu W.","year":"2014","journal-title":"J. Fluorine Chem."},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"2432","DOI":"10.1021\/cr4002879","volume":"114","author":"Wang J.","year":"2014","journal-title":"Chem. Rev."},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1080\/02678298908033211","volume":"6","author":"Suzuki Y.","year":"1989","journal-title":"Liq. Cryst."},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","first-page":"3158","DOI":"10.1002\/cbic.202100255","volume":"22","author":"Kurohara T.","year":"2021","journal-title":"Chembiochem"},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1517\/13543776.2014.940892","volume":"24","author":"Arranz\u2010Tagarro J.\u2010A.","year":"2014","journal-title":"Expert Opin. Ther. Pat."},{"key":"e_1_2_7_8_1","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1055\/s-1994-22906","volume":"1994","author":"Katagiri T.","year":"1994","journal-title":"Synlett"},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","first-page":"979","DOI":"10.1002\/chir.23127","volume":"31","author":"Wong L. W. Y.","year":"2019","journal-title":"Chirality"},{"key":"e_1_2_7_10_1","doi-asserted-by":"crossref","first-page":"4603","DOI":"10.1016\/S0040-4039(00)00643-2","volume":"41","author":"Kuroki Y.","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"e_1_2_7_11_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s43586-020-00001-2","volume":"1","author":"Bell E. L.","year":"2021","journal-title":"Nat. Rev. Methods Primers"},{"key":"e_1_2_7_12_1","doi-asserted-by":"crossref","first-page":"594","DOI":"10.1039\/D1CS00100K","volume":"51","author":"Hanefeld U.","year":"2022","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_7_13_1","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1021\/acscentsci.0c01496","volume":"7","author":"Winkler C. K.","year":"2021","journal-title":"ACS Cent. Sci."},{"key":"e_1_2_7_14_1","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/j.cbpa.2020.02.004","volume":"55","author":"Huang X.","year":"2020","journal-title":"Curr. Opin. Chem. Biol."},{"key":"e_1_2_7_15_1","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1002\/anie.202006648","volume":"60","author":"Wu S.","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","first-page":"eadh8615","DOI":"10.1126\/science.adh8615","volume":"382","author":"Buller R.","year":"2023","journal-title":"Science"},{"key":"e_1_2_7_17_1","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1007\/s12010-020-03272-3","volume":"192","author":"Jiang W.","year":"2020","journal-title":"Appl. Biochem. Biotechnol."},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1126\/science.aaz7381","volume":"367","author":"Gagnon C.","year":"2020","journal-title":"Science"},{"key":"e_1_2_7_19_1","doi-asserted-by":"crossref","first-page":"791","DOI":"10.2174\/157017912803901628","volume":"9","author":"Palomo J. M.","year":"2012","journal-title":"Curr. Org. Synth."},{"key":"e_1_2_7_20_1","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1016\/B978-0-12-395630-9.50134-1","volume-title":"Methods of Enzymatic Analysis","author":"Bergmeyer H.\u2010U.","year":"1965"},{"key":"e_1_2_7_21_1","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1002\/9780470122822.ch2","volume":"37","author":"Everse J.","year":"1973","journal-title":"Adv. Enzymol. Relat. Areas Mol. Biol."},{"key":"e_1_2_7_22_1","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/0014-5793(73)80095-X","volume":"31","author":"Holbrook J.","year":"1973","journal-title":"FEBS Lett."},{"key":"e_1_2_7_23_1","doi-asserted-by":"crossref","first-page":"830","DOI":"10.1016\/0959-440X(95)80018-2","volume":"5","author":"Lamzin V. S.","year":"1995","journal-title":"Curr. Opin. Struct. Biol."},{"key":"e_1_2_7_24_1","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/0006-291X(92)91157-L","volume":"184","author":"Kochhar S.","year":"1992","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"e_1_2_7_25_1","doi-asserted-by":"crossref","first-page":"12588","DOI":"10.1016\/S0021-9258(18)98939-8","volume":"266","author":"Taguchi H.","year":"1991","journal-title":"J. Biol. Chem."},{"key":"e_1_2_7_26_1","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1144\/gsjgs.140.1.0027","volume":"140","author":"Livingstone D.","year":"1983","journal-title":"J. Geol. Soc."},{"key":"e_1_2_7_27_1","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1186\/1471-2148-8-268","volume":"8","author":"Cristescu M. E.","year":"2008","journal-title":"BMC Evol. Biol."},{"key":"e_1_2_7_28_1","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1128\/mr.44.1.106-139.1980","volume":"44","author":"Garvie E. I.","year":"1980","journal-title":"Microbiol. Rev."},{"key":"e_1_2_7_29_1","doi-asserted-by":"crossref","first-page":"12997","DOI":"10.1038\/s41598-021-92430-6","volume":"11","author":"Wu Y.","year":"2021","journal-title":"Sci. Rep."},{"key":"e_1_2_7_30_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bbcan.2016.12.004","volume":"1868","author":"Morandi A.","year":"2017","journal-title":"Biochim. Biophys. Acta, Rev. Cancer"},{"key":"e_1_2_7_31_1","first-page":"354143","volume":"2015","author":"Gao J.\u2010L.","year":"2015","journal-title":"BioMed Res. Int."},{"key":"e_1_2_7_32_1","doi-asserted-by":"crossref","first-page":"3285","DOI":"10.1021\/jm201734r","volume":"55","author":"Ward R. A.","year":"2012","journal-title":"J. Med. Chem."},{"key":"e_1_2_7_33_1","doi-asserted-by":"crossref","first-page":"1698","DOI":"10.1016\/j.cell.2016.05.040","volume":"165","author":"Merk A.","year":"2016","journal-title":"Cell"},{"key":"e_1_2_7_34_1","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/0022-2836(81)90516-7","volume":"151","author":"Grau U. M.","year":"1981","journal-title":"J. Mol. Biol."},{"key":"e_1_2_7_35_1","doi-asserted-by":"crossref","first-page":"13155","DOI":"10.1016\/S0021-9258(18)45181-2","volume":"262","author":"Hogrefe H. H.","year":"1987","journal-title":"J. Biol. Chem."},{"key":"e_1_2_7_36_1","doi-asserted-by":"crossref","first-page":"12782","DOI":"10.1021\/jp903579x","volume":"113","author":"Swiderek K.","year":"2009","journal-title":"J. Phys. Chem. B"},{"key":"e_1_2_7_37_1","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1002\/cbic.201600288","volume":"17","author":"Li C.","year":"2016","journal-title":"Chembiochem"},{"key":"e_1_2_7_38_1","doi-asserted-by":"crossref","first-page":"1491","DOI":"10.1016\/j.enzmictec.2017.08.005","volume":"108","author":"Andree\u00dfen C.","year":"2018","journal-title":"Enzyme Microb. Technol."},{"key":"e_1_2_7_39_1","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.jbiotec.2015.05.015","volume":"207","author":"Zheng Z.","year":"2015","journal-title":"J. Biotechnol."},{"key":"e_1_2_7_40_1","doi-asserted-by":"crossref","first-page":"1214","DOI":"10.1016\/S0006-291X(73)80023-3","volume":"55","author":"Pogolotti A.","year":"1973","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"e_1_2_7_41_1","doi-asserted-by":"crossref","first-page":"1617","DOI":"10.1021\/bi00405a034","volume":"27","author":"Clarke A. R.","year":"1988","journal-title":"Biochemistry"},{"key":"e_1_2_7_42_1","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1111\/j.1432-1033.1976.tb10108.x","volume":"62","author":"Sch\u00fctte H.","year":"1976","journal-title":"Eur. J. Biochem."},{"key":"e_1_2_7_43_1","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.molcatb.2014.01.007","volume":"102","author":"Kim S.","year":"2014","journal-title":"J. Mol. Catal. B: Enzym."},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"5567","DOI":"10.1021\/jo00308a012","volume":"55","author":"Asano Y.","year":"1990","journal-title":"J. Org. Chem."},{"key":"e_1_2_7_45_1","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/j.enzmictec.2013.01.009","volume":"52","author":"Binay B.","year":"2013","journal-title":"Enzym. microb. Technol."},{"key":"e_1_2_7_46_1","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/0006-291X(89)91559-3","volume":"161","author":"Bur D.","year":"1989","journal-title":"Biochem. Biophys Res. Commun."},{"key":"e_1_2_7_47_1","doi-asserted-by":"crossref","first-page":"1541","DOI":"10.1126\/science.3201242","volume":"242","author":"Wilks H. M.","year":"1988","journal-title":"Science"},{"key":"e_1_2_7_48_1","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1016\/j.jbiotec.2018.05.011","volume":"281","author":"Li J.\u2010F.","year":"2018","journal-title":"J. Biotechnol."},{"key":"e_1_2_7_49_1","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/S0022-2836(02)00086-4","volume":"318","author":"Razeto A.","year":"2002","journal-title":"J. Mol. Biol."},{"key":"e_1_2_7_50_1","doi-asserted-by":"crossref","first-page":"3401","DOI":"10.1038\/srep03401","volume":"3","author":"Zheng Z.","year":"2013","journal-title":"Sci. Rep."},{"key":"e_1_2_7_51_1","doi-asserted-by":"crossref","first-page":"8371","DOI":"10.1021\/acs.jafc.8b02454","volume":"66","author":"Jia B.","year":"2018","journal-title":"J. agric. food Chem."},{"key":"e_1_2_7_52_1","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1093\/clinchem\/22.2.141","volume":"22","author":"McComb R. B.","year":"1976","journal-title":"Clin. Chem."}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.202500047","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,9]],"date-time":"2025-11-09T15:45:17Z","timestamp":1762703117000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.202500047"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,27]]},"references-count":51,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2025,6,3]]}},"alternative-id":["10.1002\/cbic.202500047"],"URL":"https:\/\/doi.org\/10.1002\/cbic.202500047","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,27]]},"assertion":[{"value":"2025-01-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-03-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202500047"}}