{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,28]],"date-time":"2025-11-28T12:17:53Z","timestamp":1764332273952,"version":"3.37.3"},"reference-count":19,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2014,10,9]],"date-time":"2014-10-09T00:00:00Z","timestamp":1412812800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/3.0\/"}],"funder":[{"DOI":"10.13039\/100000774","name":"Defense Threat Reduction Agency","doi-asserted-by":"publisher","award":["CB3945"],"award-info":[{"award-number":["CB3945"]}],"id":[{"id":"10.13039\/100000774","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chirality"],"published-print":{"date-parts":[[2014,12]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p>Chemical warfare nerve agents (CWNAs) are extremely toxic organophosphorus compounds that contain a chiral phosphorus center. Undirected synthesis of G\u2010type CWNAs produces stereoisomers of tabun, sarin, soman, and cyclosarin (GA, GB, GD, and GF, respectively). Analytical\u2010scale methods were developed using a supercritical fluid chromatography (SFC) system in tandem with a mass spectrometer for the separation, quantitation, and isolation of individual stereoisomers of GA, GB, GD, and GF. Screening various chiral stationary phases (CSPs) for the capacity to provide full baseline separation of the CWNAs revealed that a Regis WhelkO1 (SS) column was capable of separating the enantiomers of GA, GB, and GF, with elution of the P(+) enantiomer preceding elution of the corresponding P(\u2013) enantiomer; two WhelkO1 (SS) columns had to be connected in series to achieve complete baseline resolution. The four diastereomers of GD were also resolved using two tandem WhelkO1 (SS) columns, with complete baseline separation of the two P(+) epimers. A single WhelkO1 (RR) column with inverse stereochemistry resulted in baseline separation of the GD P(\u2013) epimers. The analytical methods described can be scaled to allow isolation of individual stereoisomers to assist in screening and development of countermeasures to organophosphorus nerve agents. <jats:italic>Chirality 26:817\u2013824, 2014<\/jats:italic>. \u00a9 2014 The Authors. <jats:italic>Chirality<\/jats:italic> published by John Wiley Periodicals, Inc.<\/jats:p>","DOI":"10.1002\/chir.22368","type":"journal-article","created":{"date-parts":[[2014,10,9]],"date-time":"2014-10-09T10:11:56Z","timestamp":1412849516000},"page":"817-824","source":"Crossref","is-referenced-by-count":10,"title":["Chiral Separation of G\u2010type Chemical Warfare Nerve Agents via Analytical Supercritical Fluid Chromatography"],"prefix":"10.1002","volume":"26","author":[{"given":"Shane A.","family":"Kasten","sequence":"first","affiliation":[{"name":"Physiology and Immunology Branch, Research Division US Army Medical Research Institute of Chemical Defense, APG, MD"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Steven","family":"Zulli","sequence":"additional","affiliation":[{"name":"Waters Corp.  New Castle DE"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jonathan L.","family":"Jones","sequence":"additional","affiliation":[{"name":"Waters Corp.  New Castle DE"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas","family":"Dephillipo","sequence":"additional","affiliation":[{"name":"Waters Corp.  Milford MA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Douglas M.","family":"Cerasoli","sequence":"additional","affiliation":[{"name":"Physiology and Immunology Branch, Research Division US Army Medical Research Institute of Chemical Defense, APG, MD"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,10,9]]},"reference":[{"volume-title":"Clinical and experimental toxicology of organophosphates and carbamates","year":"1992","author":"Ballantyne B","key":"e_1_2_6_2_1"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/nm1013-1194"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0196-0644(96)70052-5"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00154a003"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/0041-008X(84)90249-7"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/0272-0590(84)90140-4"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00286a043"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/0003-2697(85)90172-1"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.enzmictec.2005.04.004"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.toxlet.2010.03.012"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2008.08.001"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/28.5.390"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/chir.20898"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chroma.2009.10.004"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527611737"},{"volume-title":"The LC Handbook","year":"2011","author":"Technologies A","key":"e_1_2_6_17_1"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2007.08.040"},{"key":"e_1_2_6_19_1","unstructured":"D'AgostinoPAaCCL.Analysis of chemical warfare agents: general overview LC\u2010MS review in\u2010house LC\u2010ESI\u2010MS methods and open literature bibliography: Defence Research and Development Suffield (Alberta);2006."},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1093\/jat\/32.1.86"}],"container-title":["Chirality"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.22368","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchir.22368","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chir.22368","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,5]],"date-time":"2023-10-05T20:30:26Z","timestamp":1696537826000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/chir.22368"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,10,9]]},"references-count":19,"journal-issue":{"issue":"12","published-print":{"date-parts":[[2014,12]]}},"alternative-id":["10.1002\/chir.22368"],"URL":"https:\/\/doi.org\/10.1002\/chir.22368","archive":["Portico"],"relation":{},"ISSN":["0899-0042","1520-636X"],"issn-type":[{"type":"print","value":"0899-0042"},{"type":"electronic","value":"1520-636X"}],"subject":[],"published":{"date-parts":[[2014,10,9]]}}}