{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,20]],"date-time":"2025-10-20T18:35:41Z","timestamp":1760985341237,"version":"3.41.0"},"reference-count":29,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2015,9,18]],"date-time":"2015-09-18T00:00:00Z","timestamp":1442534400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2015,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A simple one\u2010dimensional<jats:sup>13<\/jats:sup>C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of \u03b1\u2010tocopherol. To achieve this the chiral solvating agent (<jats:italic>S<\/jats:italic>)\u2010(+)\u20101\u2010(9\u2010anthryl)\u20102,2,2\u2010trifluoroethanol and the compound of interest were dissolved in high concentrations in chloroform\u2010d, and the nuclear magnetic resonance (NMR) spectrum was recorded at a low temperature. The individual stereoisomers of \u03b1\u2010tocopherol were assigned by spikes of the reference compounds. The method was also applied to six other representative examples.<jats:italic>Chirality 27:850\u2013855, 2015<\/jats:italic>. \u00a9 2015 Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/chir.22535","type":"journal-article","created":{"date-parts":[[2015,9,19]],"date-time":"2015-09-19T04:27:26Z","timestamp":1442636846000},"page":"850-855","source":"Crossref","is-referenced-by-count":8,"title":["A Simple<sup>13<\/sup>C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of \u03b1\u2010Tocopherol Resolved"],"prefix":"10.1002","volume":"27","author":[{"given":"Peter P.","family":"Lankhorst","sequence":"first","affiliation":[{"name":"DSM Biotechnology Center DSM Delft Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas","family":"Netscher","sequence":"additional","affiliation":[{"name":"DSM Nutritional Products Research and Development Basel Switzerland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander L. L.","family":"Duchateau","sequence":"additional","affiliation":[{"name":"DSM Biotechnology Center DSM Delft Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2015,9,18]]},"reference":[{"volume-title":"Discrimination of chiral compounds using NMR spectroscopy","year":"2007","author":"Wenzel TJ","key":"e_1_2_5_2_1"},{"key":"e_1_2_5_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00422a061"},{"key":"e_1_2_5_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470147221.ch4"},{"key":"e_1_2_5_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-507701-9.50013-9"},{"key":"e_1_2_5_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2012.10.085"},{"key":"e_1_2_5_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04077E"},{"key":"e_1_2_5_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac402580j"},{"key":"e_1_2_5_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol403776k"},{"key":"e_1_2_5_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02535027"},{"key":"e_1_2_5_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19810640422"},{"key":"e_1_2_5_12_1","first-page":"536","article-title":"Analysis of the stereoisomers of alpha\u2010tocopheryl acetate by HPLC","volume":"15","author":"Yamagushi H","year":"1984","journal-title":"Iyakuhin Kenkyu"},{"key":"e_1_2_5_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20630"},{"key":"e_1_2_5_14_1","doi-asserted-by":"publisher","DOI":"10.3177\/jnsv.39.207"},{"key":"e_1_2_5_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/elps.201000410"},{"key":"e_1_2_5_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19900730403"},{"key":"e_1_2_5_17_1","first-page":"715","article-title":"Determination of the stereoisomers of racemic alpha\u2010tocopherol in pharmaceutical preparations by high\u2010performance liquid chromatography and gas chromatography","volume":"65","author":"Klaczkow G","year":"2008","journal-title":"Acta Pol Pharm"},{"key":"e_1_2_5_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/mrc.1270140218"},{"key":"e_1_2_5_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00264a012"},{"key":"e_1_2_5_20_1","doi-asserted-by":"crossref","first-page":"121","DOI":"10.2533\/chimia.1991.121","article-title":"(S)\u2010Trolox\u2122\u2009methyl ether: a powerful derivatizing reagent for the GC determination of the enantiomers of aliphatic alcohols","volume":"45","author":"Walther W","year":"1991","journal-title":"Chimia"},{"key":"e_1_2_5_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/3527602151.ch4"},{"key":"e_1_2_5_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200705521"},{"key":"e_1_2_5_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200705521"},{"key":"e_1_2_5_23_1","doi-asserted-by":"crossref","first-page":"163","DOI":"10.2533\/chimia.1989.163","article-title":"A practical method for the stereochemical analysis of acyclic terpenoid carbonyl\u2010compounds","volume":"43","author":"Knierzinger A","year":"1989","journal-title":"Chimia"},{"key":"e_1_2_5_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19900730432"},{"key":"e_1_2_5_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)01930-2"},{"key":"e_1_2_5_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)92418-5"},{"key":"e_1_2_5_27_1","first-page":"71","article-title":"Sulfonate leaving groups for nucleophilic substitution reactions \u2013 improved structures and procedures","volume":"7","author":"Netscher T","year":"2003","journal-title":"Recent Res Dev Org Chem"},{"key":"e_1_2_5_28_1","first-page":"50","article-title":"Improved carbon\u2010carbon linking by controlled copper catalysis","volume":"86","author":"Fouquet G","year":"1974","journal-title":"Angew Chem"},{"key":"e_1_2_5_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19740862102"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.22535","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.22535","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,30]],"date-time":"2025-05-30T18:26:29Z","timestamp":1748629589000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.22535"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,9,18]]},"references-count":29,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2015,11]]}},"alternative-id":["10.1002\/chir.22535"],"URL":"https:\/\/doi.org\/10.1002\/chir.22535","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"type":"print","value":"0899-0042"},{"type":"electronic","value":"1520-636X"}],"subject":[],"published":{"date-parts":[[2015,9,18]]}}}