RT Journal Article
SR Electronic
T1 Synthesis and elimination reactions of methylsulfonium ions formed from styrene oxide and methylthio compounds related to methionine and cysteine.
JF Drug Metabolism and Disposition
JO Drug Metab Dispos
FD American Society for Pharmacology and Experimental Therapeutics
SP 297
OP 303
VO 12
IS 3
A1 L S Sheng
A1 E C Horning
A1 M G Horning
YR 1984
UL http://dmd.aspetjournals.org/content/12/3/297.abstract
AB 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.