The influence of steric interactions on the conformation and biology of oxytocin. Synthesis and analysis of penicillamine6-oxytocin and penicillamine6-5-tert-butylproline7-oxytocin analogs

Journal of Peptide Research

Volumn 58, Issue 3, 2001, Pages 263-273

  Belec L ^a   Maletinska, L ^a   Slaninova J ^a   Lubell, W D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

5 tert butylproline; Oxytocin; Penicillamine; Proline; Prolyl amide isomers; Steric interactions

Indexed keywords

OXYTOCIN; OXYTOCIN ANTAGONIST; OXYTOCIN DERIVATIVE; PENICILLAMINE;

AGONIST; AMINO ACID SUBSTITUTION; ARTICLE; BINDING AFFINITY; HORMONE ACTION; ISOMERISM; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; STEREOCHEMISTRY; UTERUS CONTRACTION;

ANIMALS; FEMALE; MOLECULAR CONFORMATION; OXYTOCIN; PENICILLAMINE; PROLINE; RATS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; UTERUS;

EID: 0034840834     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.2001.00932.x     Document Type: Article

References (29)

1. Syntheses and conformations of somatostatin-related cyclic hexapeptides incorporating specific α- and β-methylated residues
2. Analogues of angiotensin II with restricted conformational freedom, including a new antagonist
3. 5]enkephalin
4. Novel conformational distributions of methylproline peptides
5. Pro-D-NMe-amino acid and D-Pro-NMe-amino acid. Simple, efficient reverse-turn constraints
6. Steric effects on the amide isomer equilibrium of prolyl peptides. Synthesis and conformational analysis of N-acetyl-5-tert-butylproline N′-methylamides
7. -1
8. 7 amide cis-isomer population
9. Conformational aspects of differences in requirements for oxytocin and vasopressin receptors
10. Synthesis and some pharmacological properties of 6-L-penicillamine-oxytocin
11. Synthesis of 1-L-penicillamine-oxytocin, 1-D-penicillamine-oxytocin, and 1-deaminopenicillamine-oxytocin, potent inhibitors of the oxytocic response of oxytocin
12. Synthesis, pharmacological, conformational, and dynamic studies of the potent hormone antagonists [1-penicillamine, 4-threonine]-oxytocin and [1-penicillamine, 2-phenylalanine, 4-threonine]-oxytocin
13. Conformational study of the potent peptide hormone antagonist [1-penicillamine, 2-leucine]oxytocin in aqueous solution
14. Conformational studies of neurohypophyseal hormones and inhibitors using high resolution NMR spectroscopy
15. Relative conformational rigidity in oxytocin and [1-penicillamine]-oxytocin: A proposal for the relationship of conformational flexibility to peptide hormone agonism and antagonism
16. Conformational studies of the potent oxytocin antagonists, [1-penicillamine, 4-threonine]-oxytocin and [1-penicillamine, 2-phenylalanine, 4-threonine]-oxytocin
17. 6 interchange in nonselective and selective vassopressin and oxytocin antagonists
18. 1-((7, 7-Dimethyl-2 (S)-(2(S)-amino-4-(methylsulfonyl) butyramido)bicyclo[2.2.1]-heptan-1(S)-yl)methyl)sulfonyl)-4-(2-methylphenyl) piperazine (L-368, 899): An orally bioavailable, non-peptide oxytocin antagonist with potential utility for managing preterm labor
19. Structure determination of a tetrasaccharide transient nuclear Overhauser effects in the rotating frame
20. The use of steric interactions to control peptide turn geometry. Synthesis of type VI β-turn mimics with 5-tert-butylproline
21. Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction
22. A comparison of acid labile linkage agents for the synthesis of peptide C-terminal amides
23. Disulfide bond formation in peptides by dimethyl sulfoxide. Scope applications
24. Chromatographic detection of thiols, disulfides, and thioesters with 5, 5′-dithiobis(2-nitrobenzoic acid)
25. 7-oxytocin analogues and their influence on conformation and biological activity
26. Partial agonism: Mechanisms based on ligand-receptor interactions and on stimulus-response coupling
27. A convenient preparation of S-benzhydryl- and S-trityl-L-cysteine
28. In situ generation of Fmoc amino acid chlorides for extremely difficult couplings to sterically hindered secondary amines in solid-phase peptide synthesis