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Acetylation of Amino and Tyrosine Hydroxyl Groups

PREPARATION OF INHIBITORS OF OXYTOCIN WITH NO INTRINSIC ACTIVITY ON THE ISOLATED UTERUS

From the ¹ From the National Institute for Medical Research, Mill Hill, London, N.W. 7, England

Some reactions of acetic anhydride with model compounds containing amino and phenolic hydroxyl groups have been studied. From the observed reaction rates, optimal experimental conditions were selected for acetylation of the terminal amino group and the tyrosine hydroxyl group of oxytocin. Two new analogues, N-acetyl-O-acetyloxytocin and N-carbamyl-O-acetyloxytocin have been prepared. Evidence was obtained concerning the sites of reaction and degree of purity. Neither of these analogues causes contraction of the isolated rat uterus but both inhibit the action of oxytocin. The analogues are stable under physiological conditions of temperature and pH. On treatment with hydroxylamine, N-acetyl-O-acetyloxytocin gave rise to N-acetyloxytocin, and N-carbamyl-O-acetyloxytocin gave rise to N-carbamyloxytocin, the reactions being accompanied by disappearance of the inhibitory properties and appearance of oxytocic activity. The preparation of ¹⁴C-labeled N-acetyl-O-acetyloxytocin is described.

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