Abstract
Sulfur Mustard (SM) is a blistering agent used as a chemical weapon. Glutathione (GSH) is involved in the β-lyase degradation pathway of SM and recently, bioadducts between SM and GSH were observed in vitro. While these bioadducts have never been isolated from in vivo tests or real poisoning with SM, they could be of interest as potential future biomarkers for the retrospective validation of exposure. We herein report the synthesis of different observed and new potential GSH–SM bioadducts as reference materials for analytical investigation. Two distinct approaches were investigated: a building-block pathway and the direct reaction with GSH. The availability of these references will aid future studies and may lead to the discovery of new GSH–SM biomarkers.
Highlights
Sulfur Mustard (SM) or 2,20-dichloroethyl sul de was synthesized for the rst time in 1822 by Despretz and its harmful properties were described 38 years later by Guthrie.1SM was used as a chemical weapon for the rst time in 1917 during the battle of Ypres, Belgium, which led to the name Yperite
In 1997, the development, production, stockpile and use of SM and other chemical weapons were prohibited under the Chemical Weapons Convention (CWC), which is enforced by the Organisation for the Prohibition of Chemical Weapons (OPCW)
SM acts as an irritant and a er a latency period of 2 to 24 hours, blisters occur on the skin, which can turn into skin necrosis
Summary
Sulfur Mustard (SM) or 2,20-dichloroethyl sul de was synthesized for the rst time in 1822 by Despretz and its harmful properties were described 38 years later by Guthrie.1SM was used as a chemical weapon for the rst time in 1917 during the battle of Ypres, Belgium, which led to the name Yperite. GSH was alkylated with 2 under slightly basic conditions.15 The resulting S-tBuOETE–GSH 3 was puri ed by reversed phase ash chromatography and obtained in good yield and purity. With the direct alkylation approach 4 was obtained in two steps from GSH with 28% yield and >95% purity.
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