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. 1976 Sep;73(9):3054–3058. doi: 10.1073/pnas.73.9.3054

Importance of the third amino acid residue of oxytocin for its action on isolated rat uterus: study of relationship between hormone conformation and activity.

R Walter, C W Smith, J Roy
PMCID: PMC430926  PMID: 184456

Abstract

In a continued effort to relate the three-dimensional structure of a peptide hormone to its biological activity, the dose-response relationships of [3-phenylalanine] oxytocin (oxypressin), with an aromatic amino acid residue in position 3, and [3-beta-cyclohexylalanine]oxytocin, with an aliphatic amino acid residue to position 3, were determined in the rat uterine assay in vitro and compared to that of oxytocin. Oxypressin has not only a lower affinity for the smooth muscle receptor than the natural hormone, but also a decreased maximal response (efficacy). [3-beta-Cyclohexylalanine]oxytocin exhibits an even lower affinity than oxypressin, but retains the same maximal response as oxytocin. A reorientation of the tyrosine sidechain, caused by the presence of a neighboring aromatic sidechain in position 3, away from the surface of the 20-membered ring is though to remove the phenolic hydroxyl group from its optimal position in the "active center" of oxytocin and give rise to the reduced efficacy of oxypressin.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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