{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T22:48:45Z","timestamp":1774392525076,"version":"3.50.1"},"reference-count":31,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2024,1,17]],"date-time":"2024-01-17T00:00:00Z","timestamp":1705449600000},"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":[[2024,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(<jats:italic>S<\/jats:italic>)\u2010Lifitegrast (LFT) is the novel integrin antagonist, approved by the Food and drug administration, to treat signs and symptoms of dry eye disease. Synthesis of racemic LFT, preparative and analytical enantiomer separation, and chiral interconversion studies are lacking in the literature. Hence, in our study, synthesis of LFT racemate, chiral preparative purification procedure of enantiomer, and comprehensive analytical advancements are focused on rapid enantioselective separation and pH\u2010dependent chiral interconversion studies. The synthesis of LFT racemate employed 2\u2010amino\u20103\u2010(3\u2010(methylsulfonyl)phenyl)propanoic acid hydrochloride and 2\u2010(benzofuran\u20106\u2010carbonyl)\u20105,7\u2010dichloro\u20101,2,3,4\u2010tetrahydroisoquinoline\u20106\u2010carbonyl chloride as starting materials. (<jats:italic>R<\/jats:italic>)\u2010LFT was isolated from the racemate by preparative chiral HPLC and characterized using Q\u2010TOF, FT\u2010IR, NMR spectroscopy, and chiral HPLC. The purity of (<jats:italic>R<\/jats:italic>)\u2010LFT was determined to have an enantiomeric excess of 99.12%. A precise, accurate, rapid HPLC\u2010DAD enantioselective analytical method has been developed on Chiralpak IC [tris(3,5\u2010dichloro phenyl carbamate) immobilized on cellulose] using water and methanol as mobile phase. The chiral interconversion study reveals 0.22% and 0.21% of interconversion of (<jats:italic>S<\/jats:italic>)\u2010LFT into (<jats:italic>R<\/jats:italic>)\u2010LFT at 80\u00b0C in pH\u00a07.4 and 9.5 buffers, respectively, on the 24th day. An alternative route to enantioselective synthesis of LFT enantiomers by chromatographic separation is proposed. The validated enantioselective HPLC method will help to test the regular quality control samples.<\/jats:p>","DOI":"10.1002\/chir.23636","type":"journal-article","created":{"date-parts":[[2024,1,18]],"date-time":"2024-01-18T06:41:06Z","timestamp":1705560066000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Enantioselective polar\u2010organic mode high\u2010performance liquid chromatographic separation of lifitegrast on immobilized polysaccharide stationary phase and its application to pH\u2010dependent chiral interconversion studies"],"prefix":"10.1002","volume":"36","author":[{"given":"Jony Susanna","family":"Kandula","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Analysis National Institute of Pharmaceutical Education and Research, Guwahati  Guwahati Assam India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7320-9329","authenticated-orcid":false,"given":"Veera Venkata Satya Prasanna Kumari","family":"Rayala","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis National Institute of Pharmaceutical Education and Research, Guwahati  Guwahati Assam India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Keyur","family":"Parmar","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis National Institute of Pharmaceutical Education and Research, Guwahati  Guwahati Assam India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Veerabhadra Swamy","family":"Ponnapalli","sequence":"additional","affiliation":[{"name":"Daicel Chiral Technologies (India) Private Limited  Hyderabad Telangana India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mahendar","family":"Gantala","sequence":"additional","affiliation":[{"name":"Daicel Chiral Technologies (India) Private Limited  Hyderabad Telangana India"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9095-5414","authenticated-orcid":false,"given":"Radhakrishnanand","family":"P.","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Analysis National Institute of Pharmaceutical Education and Research, Guwahati  Guwahati Assam India"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,1,17]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.2174\/1381612822666160614012634"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/jcm11175014"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.4103\/0976\u2010500X.195920"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jtos.2016.01.001"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ml2002482"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.8b00260"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201904846"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.2174\/1389200043335360"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2004.01.035"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.10077"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpba.2009.05.005"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.1052"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1007\/128_2013_453"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00198a101"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.530050302"},{"key":"e_1_2_7_17_1","unstructured":"ICH Q6A specifications: test procedures and acceptance criteria for new drug substances and new drug products: chemical substances. 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