Abstract:[5‐β‐Malamidic acid] oxytocin was synthesized to study the importance of the hydrogen bond between the C=O of Tyr2 and the peptide N‐H of Asn5 for the stabilization of a biologically functional conformation of oxytocin. This analog lacks the peptide N‐H at residue 5 required for the formation of a hydrogen bond with the C=O of Tyr2. [5‐β‐Malamidic acid] oxytocin exhibited 45.1 ± 2.5 U/mg and 65.6 ± 5.9 U/mg of uterotonic activity, in vitro, in the absence and in the presence, respectively, of Mg2+, 147 ± 14 U/… Show more
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