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- W2100521567 abstract "In an attempt to see whether the C=O and the NH2 of CONH2 of asparagine5 and glycinamide9 are both essential for biological activity, [5-beta-cyanoalanine] oxytocin and [9-alpha-aminoacetonitrile] oxytocin have been synthesized. Each of these analogs contains a nitrile group in place of the carboxamide group of Asn5 and GlyNH92 respectively; the nitrile group can simulate the carbonyl portion of the carboxamide, but lacks the hydrogen-bond donating capacity of its NH2 portion. Substitution of a nitrile group produced opposite biological effects in the 5 and the 9 positions; the 5-substituted analog showed very low activities (less than 3% of those of oxytocin) while the 9-substituted analog showed extremely high activities (with an in vivo uterine activity of 906 U/mg almost twice that of oxytocin). The results clearly suggest that the mechanisms of interaction of the carboxamide groups with the receptor sites are different for residues 5 and 9." @default.
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- W2100521567 date "2009-01-12" @default.
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- W2100521567 title "Role of the carboxamide groups of the asparagine and glycinamide residues of oxytocin. Syntheses and biological properties of [5-β-cyanoalanine] oxytocin and [9-α-aminoacetonitrile] oxytocin" @default.
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- W2100521567 doi "https://doi.org/10.1111/j.1399-3011.1983.tb02125.x" @default.
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