title: Relative conformational rigidity in oxytocin and (1-penicillamine)-oxytocin: a proposal for the relationship of conformational flexibility to peptide hormone agonism and antagonism.
abstract: A comparative study of the proton and carbon-13 nuclear magnetic resonance spectral parameters of the peptide hormone oxytocin and of its competitive inhibitor [1-L-penicillamine]oxytocin has been made, and the results analyzed in terms of comparative conformational and dynamic properties. The results indicate that oxytocin has a flexible conformation, while [1-L-penicillamine]oxytocin has a more restricted conformation. The results provide a framework for understanding the mechanism of peptide hormone agonism and antagonism for these compounds, and an approach for understanding some features of the interaction of the hormone and related compounds with their receptor.
mesh_terms: D001665:Binding Sites; D009682:Magnetic Resonance Spectroscopy; D010121:Oxytocin / Q000031:analogs & derivatives* / Q000037:antagonists & inhibitors; D010396:Penicillamine; D011485:Protein Binding; D011487:Protein Conformation
chemical_list: D010121:Oxytocin; D010396:Penicillamine
references.citation: J Am Chem Soc. 1976 Sep 29;98(20):6408-10
references.pmid: 965654
references.citation: J Org Chem. 1976 Apr 16;41(8):1353-8
references.pmid: 1263005
references.citation: J Mol Biol. 1973 Oct 25;80(2):277-95
references.pmid: 4763987
references.citation: Proc Natl Acad Sci U S A. 1972 Dec;69(12):3629-33
references.pmid: 4509324
references.citation: J Am Chem Soc. 1972 Apr 19;94(8):2851-4
references.pmid: 5017422
references.citation: Biochemistry. 1973 Dec 18;12(26):5294-304
references.pmid: 4760494
references.citation: J Mol Biol. 1973 Sep 25;79(3):555-75
references.pmid: 4758065
references.citation: Proc Natl Acad Sci U S A. 1973 Jul;70(7):2086-90
references.pmid: 4516207
references.citation: Proc Natl Acad Sci U S A. 1973 Dec;70(12):3806-9
references.pmid: 4521206
references.citation: Nat New Biol. 1971 Jul 28;232(30):108-10
references.pmid: 5284945
references.citation: Proc Natl Acad Sci U S A. 1970 Sep;67(1):239-46
references.pmid: 5272315
references.citation: Biochem Biophys Res Commun. 1969 Jul 23;36(2):194-202
references.pmid: 5799638
references.citation: FEBS Lett. 1976 Feb 1;62(1):50-6
references.pmid: 2504
references.citation: Biochemistry. 1976 Mar 9;15(5):1111-9
references.pmid: 1252430
references.citation: J Am Chem Soc. 1974 Apr 3;96(7):2289-91
references.pmid: 4364949
references.citation: Physiol Rev. 1975 Oct;55(4):489-536
references.pmid: 171691
references.citation: Biochemistry. 1976 Jan 13;15(1):234-42
references.pmid: 2282
references.citation: J Theor Biol. 1975 Jul;52(1):223-30
references.pmid: 168441
references.citation: J Pharmacol Exp Ther. 1974 Jul;190(1):77-87
references.pmid: 4847314
references.citation: J Med Chem. 1974 Sep;17(9):969-72
references.pmid: 4855467
references.citation: J Med Chem. 1973 Jun;16(6):620-3
references.pmid: 4714992
references.citation: J Med Chem. 1972 Feb;15(2):123-6
references.pmid: 5008235
references.citation: Nature. 1975 Feb 27;253(5494):753-5
references.pmid: 1113874
references.citation: J Med Chem. 1975 Mar;18(3):284-7
references.pmid: 1133819
references.citation: J Am Chem Soc. 1970 Feb 11;92(3):677-80
references.pmid: 5460748
references.citation: Biochim Biophys Acta. 1970 Feb 17;200(2):395-403
references.pmid: 5416128