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This system can also be used for catalytic deuteration of <jats:sc>D<\/jats:sc>\u2010alanine with retention of stereochemistry to give deuterated <jats:sc>D<\/jats:sc>\u2010alanine. Thus a racemic mixture of alanine can be catalytically deuterated to give an enantiomeric excess of deuterated <jats:sc>D<\/jats:sc>\u2010alanine. While catalytic deracemization of alanine is forbidden by the second law of thermodynamics, this system can be used for catalytic deracemization of alanine with deuteration. Such green and biomimetic approach to catalytic stereocontrol provides insights into efficient amino acid transformations.<\/jats:p>","DOI":"10.1002\/anie.201503616","type":"journal-article","created":{"date-parts":[[2015,6,27]],"date-time":"2015-06-27T09:39:18Z","timestamp":1435397958000},"page":"9381-9385","source":"Crossref","is-referenced-by-count":58,"title":["Catalytic Stereoinversion of <scp>L<\/scp>\u2010Alanine to Deuterated <scp>D<\/scp>\u2010Alanine"],"prefix":"10.1002","volume":"54","author":[{"given":"Kimia","family":"Moozeh","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Soon Mog","family":"So","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jik","family":"Chin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,6,26]]},"reference":[{"key":"e_1_2_3_1_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101073"},{"key":"e_1_2_3_2_2","unstructured":"\u00a0"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1742-4658.2008.06516.x"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar000056y"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.200900245"},{"key":"e_1_2_3_6_2","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature10702"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705468"},{"key":"e_1_2_3_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705468"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.11.004"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm4007998"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/45751"},{"key":"e_1_2_3_12_2","unstructured":"\u00a0"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067724g"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307410"},{"key":"e_1_2_3_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307410"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201407944"},{"key":"e_1_2_3_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201407944"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00726-013-1580-3"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ob40541a"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2013.02.022"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067995r"},{"key":"e_1_2_3_20_2","unstructured":"\u00a0"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049579h"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja067643k"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00851a026"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbpa.2009.11.027"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1007\/128_2006_094"},{"key":"e_1_2_3_26_2","unstructured":"\u00a0"},{"key":"e_1_2_3_27_2","first-page":"77","volume":"40","author":"Ooi T.","year":"2007","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0300625"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar030058t"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973174y"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201503616","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201503616","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T05:33:06Z","timestamp":1697434386000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201503616"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,6,26]]},"references-count":33,"journal-issue":{"issue":"32","published-print":{"date-parts":[[2015,8,3]]}},"alternative-id":["10.1002\/anie.201503616"],"URL":"https:\/\/doi.org\/10.1002\/anie.201503616","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,6,26]]}}}