Chiral Separation of G-type Chemical Warfare Nerve Agents via Analytical Supercritical Fluid Chromatography: SEPARATION OF G-TYPE CHEMICAL WARFARE NERVE AGENTS

Kasten, Shane A.; Zulli, Steven; Jones, Jonathan L.; Dephillipo, Thomas; Cerasoli, Douglas M.

doi:10.1002/chir.22368

Chiral Separation of G-type Chemical Warfare Nerve Agents via Analytical Supercritical Fluid Chromatography: SEPARATION OF G-TYPE CHEMICAL WARFARE NERVE AGENTS

Journal Article · Thu Oct 09 00:00:00 EDT 2014 · Chirality

DOI:https://doi.org/10.1002/chir.22368· OSTI ID:1623515

Kasten, Shane A. ^[1]; Zulli, Steven ^[2]; Jones, Jonathan L. ^[2]; Dephillipo, Thomas ^[3]; Cerasoli, Douglas M. ^[4]

US Army Medical Research Inst. of Chemical Defense, Aberdeen Proving Ground, MD (United States). Research Division. Physiology and Immunology Branch; DOE/OSTI
Waters Corp., New Castle, DE (United States)
Waters Corp., Milford MA (United States)
US Army Medical Research Inst. of Chemical Defense, Aberdeen Proving Ground, MD (United States). Research Division. Physiology and Immunology Branch

Chemical warfare nerve agents (CWNAs) are extremely toxic organophosphorus compounds that contain a chiral phosphorus center. Undirected synthesis of G-type CWNAs produces stereoisomers of tabun, sarin, soman, and cyclosarin (GA, GB, GD, and GF, respectively). Analytical-scale 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(–) 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(–) 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

View Accepted Manuscript (DOE)

Research Organization:: Oak Ridge Institute for Science and Education (ORISE), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0014664

OSTI ID:: 1623515

Journal Information:: Chirality, Journal Name: Chirality Journal Issue: 12 Vol. 26; ISSN 0899-0042

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

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Chiral Separation of G-type Chemical Warfare Nerve Agents via Analytical Supercritical Fluid Chromatography: SEPARATION OF G-TYPE CHEMICAL WARFARE NERVE AGENTS

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