Synthesis and elimination reactions of methylsulfonium ions formed from styrene oxide and methylthio compounds related to methionine and cysteine.
Methylsulfonium compounds were prepared through the nucleophilic addition of a number of methylthio reagents to styrene oxide. In the absence of water, methylsulfonium ions from styrene oxide were converted to 2-hydroxy-1-methylthio-1-phenylethane (I) and 1-hydroxy-2-methylthio-1-phenylethane (II) by brief heating. In the presence of water, the glycol 1,2- dihydroxyphenylethane (III) was obtained along with I and II. The addition and elimination reactions were combined in sequences that were carried out in an organic solvent (acetone) or in aqueous solutions containing acetone or methanol. With L-methionine as the reagent, both reactions proceeded in sequence at 37 degrees C in water/methanol (80:20) to give I, II, and III as reaction products. These methods can be used to prepare the methylthio metabolites of styrene oxide.
D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000031:analogs & derivatives*; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D007700:Kinetics; D013058:Mass Spectrometry; D008715:Methionine / Q000031:analogs & derivatives*; D009861:Onium Compounds; D013452:Sulfonium Compounds
D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D009861:Onium Compounds; D013452:Sulfonium Compounds; C013690:styrene oxide; D008715:Methionine; D003545:Cysteine