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- W1582893091 abstract "Myleran and 1:4-dibromobutane react with L-cysteine at pH 8 to form the S-β-l-alanyltetrahydrothiophenium ion, and smaller quantities of S-di-l-cysteinylbutane and S-(4-hydroxybutyl)-l-cysteine. The chemical properties of the sulphonium ion are reported : (a) In the presence of aqueous alkali it rapidly decomposes to tetrahydrothiophene and aminoacrylic acid (in tautomeric equilibrium with iminopyruvic acid); (b) Electrolysis yields tetrahydrothiophene and alanine; (c) Thermal decomposition yields mainly tetrahydrothiophene; (d) Virtually no reaction occurs with cysteine at pH 7 or less; (e) At pH 8–9 it reacts rapidly and almost quantitatively with cysteine yielding S-dicysteinylbutane; (f) At pH > 10 in the presence of cysteine preferential reaction occurs with the hydroxyl ion yielding tetrahydrothiophene and aminoacrylic acid. Myleran reacts with glutathione in water or in aqueous acetone at pH > 8 yielding 30–35 per cent tetrahydrothiophene and bound lanthionine (but no bound S-dicysteinylbutane or S-hydroxybutylcysteine). Possible mechanisms for these reactions are discussed. Reduced keratin and egg albumin react with Myleran in the presence of alkali to yield tetrahydrothiophene. Myleran reacts with β-mercaptoethylamine to form the (S-(β-aminoethyl)) tetrahydrothiophenium ion, and with thioglycolic acid in the presence of alkali to yield tetrahydrothiophene. The possible relevance of these results to the metabolism of Myleran is discussed." @default.
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- W1582893091 date "1961-06-01" @default.
- W1582893091 modified "2023-09-25" @default.
- W1582893091 title "The mode of action of alkylating agents—II" @default.
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- W1582893091 doi "https://doi.org/10.1016/0006-2952(61)90132-0" @default.
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