Methionine sulphoximine (I, R ═ CH2CH2CH(NH2)COOH, R' ═ CH3) can be synthesized by the action of hydrazoic acid on methionine sulphoxide in the presence of concentrated sul-phuric acid as a catalyst and is shown to be identical with the toxic factor isolated from nitrogen trichloride-treated proteins. S-methylcysteine sulphoximine (I, R ═ -CH2CH(NH2)COOH, R' ═ CH3) and dimethyl. sulphoximine (I, R, R' ═ CH3) are prepared by a similar method from the corresponding sulphoxides; in rabbits, S-methylcysteine sulphoximine does not produce the toxic symptoms obtained with methionine sulphoximine. Possible mechanisms are discussed for the reaction between hydrazoic acid and a sulphoxide.
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Bentley et al. (1951) studied this question.
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