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The peptide bond between Pro‐Leu or Leu‐Gly in Pro‐Leu‐Gly‐NH2 was replaced by a CH2‐NH function. The 1H and 13C n.m.r. studies demonstrated that HCl·Pro‐Leu (CH2‐NH)Gly‐NH2 10 adopted a conformation in DMSO that is similar to the previously postulated β‐turn for the natural hormone. This was not the case for the other analogue. In vivo tests on 10 revealed an activity approximately equal to the natural compound and an increased toxicity.

Analogs of deamino-oxytocin and deamino-oxypressin containing a CH2-NH group instead of an amide bond between positions 8 and 9 were synthesized. All tested compounds exhibit significantly lowered biological activities.

ChemInform Abstract (synthesized using standard methods).