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

Journal Article · · Chirality
DOI:https://doi.org/10.1002/chir.22368· OSTI ID:1623515
 [1];  [2];  [2];  [3];  [1]
  1. US Army Medical Research Inst. of Chemical Defense, Aberdeen Proving Ground, MD (United States). Research Division. Physiology and Immunology Branch
  2. Waters Corp., New Castle, DE (United States)
  3. Waters Corp., Milford MA (United States)
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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

Research Organization:
Oak Ridge Inst. 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, Vol. 26, Issue 12; ISSN 0899-0042
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

References (16)

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Chromatographic resolution, characterisation and quantification of VX enantiomers in hemolysed swine blood samples journal September 2008
Development and application of procedures for the highly sensitive quantification of cyclosarin enantiomers in hemolysed swine blood samples journal November 2007
Isolation, in vitro activity, and acute toxicity in mice of the four stereoisomers of soman journal April 1984
Isolation, anticholinesterase properties, and acute toxicity in mice of the four stereoisomers of the nerve agent soman journal January 1984
Chromatographic preparation and kinetic analysis of interactions between tabun enantiomers and acetylcholinesterase journal June 2010
Analysis of the Enantiomers of VX Using Normal-Phase Chiral Liquid Chromatography with Atmospheric Pressure Chemical Ionization-Mass Spectrometry journal July 2004
Chiral separation of neonicotinoid insecticides by polysaccharide-type stationary phases using high-performance liquid chromatography and supercritical fluid chromatography journal September 2010
Systematic evaluation of new chiral stationary phases for supercritical fluid chromatography using a standard racemate library journal February 2010
Enantiospecific complexation gas chromatography of nerve agents. Isolation and properties of the enantiomers of ethyl N,N-dimethylphosphoramidocyanidate (tabun) journal December 1986
Stabilization and gas chromatographic analysis of the four stereoisomers of 1,2,2-trimethylpropyl methylphosphonofluoridate (soman) in rat blood journal December 1985
A Gas Chromatographic-Mass Spectrometric Approach to Examining Stereoselective Interaction of Human Plasma Proteins with Soman* journal January 2008
Report on 640 Victims of the Tokyo Subway Sarin Attack journal August 1996
Syrian gas attack reinforces need for better anti-sarin drugs journal October 2013
Stereospecificity in the enzymatic hydrolysis of cyclosarin (GF) journal October 2005
Isolation, in Vitro Activity, and Acute Toxicity in Mice of the Four Stereoisomers of Soman journal January 1984

Cited By (1)

Analysis of stereoisomers of chiral drug by mass spectrometry journal February 2018

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