Restricted accessResearch articleFirst published online 2019-10-03
The reaction of L-cysteine,L-cysteine hydrochloride and glutathione with arsonolipids (2,3-diacyloxypropylarsonic acids) and their arsenoso derivatives
From the arsonolipids (2,3-diacyloxypropylarsonic acids, 1) the stearoyl and palmitoyl are not reduced by ascorbic acid/iodine in methanol while the myristoyl and lauroyl arsonolipids are reduced to the arsenoso compounds 3. The reaction of arsenoso compounds 3 and of arsonolipids 1 with L-cysteine (cysSH), L-cysteine hydrochloride (cysSH·HCl) and glutathione (GSH) under various conditions was studied. Lipo-dithioarsonites [R-As(SR′)2] 4 have been isolated with GSH with both lipids 1 and 3. The product 4 was obtained only from 3 and cysSH. The salt cysSH·HCl reacted with 3 in methanol but gave it back on attempts at isolation of 4, while in DMSO unknown products were obtained. The arsonolipids 1 can be components of biological membranes and all lipo-dithioarsonites 4 prepared were insoluble in water and once formed must remain anchored in a membrane, thus altering its properties.
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