Novel strategy for the synthesis of template-assembled analogues of rat relaxin

Journal of Peptide Science

Volumn 6, Issue 5, 2000, Pages 235-242

  Mathieu, Marc N ^a   Wade, John D ^a   Tan, Yean Yeow ^a,b   Summers, Roger J ^b   Tregear, Geoffrey W ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

Antagonist; Chemoselective ligation; Rat isolated atrial bioassay; Rat relaxin; Template assembled peptide

Indexed keywords

GLYCINE; LYSINE; MERCAPTAMINE; PROLINE; RELAXIN; SULFIDE;

ALPHA HELIX; AMINO TERMINAL SEQUENCE; ANIMAL TISSUE; ARTICLE; CARBOXY TERMINAL SEQUENCE; COMPETITIVE INHIBITION; CONTROLLED STUDY; ENZYME ACTIVE SITE; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; RAT; STEREOSPECIFICITY;

ANIMALS; BIOLOGICAL ASSAY; CIRCULAR DICHROISM; PEPTIDES; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; RATS; RELAXIN; TIME FACTORS;

EID: 0034059760     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(200005)6:5<235::AID-PSC247>3.0.CO;2-J     Document Type: Article

References (21)

1. Sherwood OD. In The Physiology of Reproduction (2nd edition), Knobil E, Neill JD (eds). Raven Press: New York, 1994; 861-1009.
2. Eigenbrot C, Randal M, Quan C, Burnier J, O'Connell L, Rinderknecht E, Kossiakoff AA. X-ray structure of human relaxin at 1.5 Ȧ. J. Mol. Biol. 1991; 221: 15-21.
3. Büllesbach EE, Yang S, Schwabe C. The receptor-binding site of human relaxin II. J. Mol. Biol. 1992; 267: 22957-22960.
4. Wade JD, Tregear GW. Relaxin. Methods Enzymol. 1997; 289: 637-646.
5. Kakouris H, Eddie LW, Summers RJ. Cardiac effects of relaxin in rats. Lancet 1992; 339: 1076-1078.
6. Weisinger RS, Burns P, Eddie LW, Wintour EM. Relaxin alters the plasma osmolality-arginine vasopressin relationship in the rat. J. Endocrinol. 1993; 137: 505-510.
7. Braisted AC, Wells JA. Minimizing a binding domain from protein A. Proc. Natl. Acad. Sci. USA 1996; 93: 5688-5692.
8. Mutter M, Vuilleumier S. A chemical approach to protein design: template assembled synthetic proteins (TASP). Angew. Chem. Int. Ed. Engl. 1989; 28: 535-554.
9. Mutter M, Tuchscherer G. Non-native architectures in protein design and mimicry. Cell. Mol. Life Sci. 1997; 53: 851-863.
10. Wong AK, Jacobsen MP, Winzor DJ, Fairlie DP. Template assembled synthetic proteins (TASPs). Are template size, shape, and directionality important in formation of four-helix bundles? J. Am. Chem. Soc. 1998; 120: 3836-3841.
11. Zhang L, Tam JP. Thiazolidine formation as a general and site-specific conjugation method for synthetic peptides and proteins. Anal. Biochem. 1996; 233: 87-93.
12. Tan YY, Wade JD, Tregear GW, Summers RJ. Comparison of relaxin receptors in rat isolated atria and uterus by use of synthetic and native analogues. Brit. J. Pharmacol. 1998; 123: 762-770.
13. Schnölzer M, Alewood P, Jones P, Alewood D, Kent SBH. 'In situ' neutralization in Boc chemistry solid phase peptide synthesis: rapid high yield assembly of difficult sequences. Int. J. Peptide Protein Res. 1992; 40: 180-193.
14. Robey FA, Fields RL. Automated synthesis of N-bromoacetyl-modified peptides for the preparation of synthetic peptide polymers, peptide-protein conjugates, and cyclic peptides. Anal. Biochem. 1989; 177: 373-377.
15. Grouzmann E, Buclin T, Martire M, Cannizzaro C, Doerner B, Razaname A, Mutter M. Characterization of a selective antagonist of neuropeptide Y at the Y2 receptor. J. Mol. Biol. 1997; 272: 7699-7706.
16. Dawson PE, Kent SBH. Convenient total synthesis of a 4-helix TASP molecule by chemoselective ligation. J. Am. Chem. Soc. 1993; 115: 7263-7266.
17. Englebretsen DR, Garnham BG, Bergman DA, Alewood PF. A novel thioether linker: chemical synthesis of a HIV-1 protease analogue by thioether ligation. Tetrahedron Lett. 1995; 36: 8871-8874.
18. Tregear GW, Du Y-C, Kemp B, Borjesson BW, Scanlon D, Niall H. In Relaxin, Bryant-Greenwood GD, Niall HD, Greenwood FC (eds). Elsevier-North Holland: Amsterdam, 1981; 151-164.
19. Du Y-C, Minasian E, Tregear GW, Leach SJ. Circular dichroism studies of relaxin and insulin peptide chains. Int. J. Peptide Protein Res. 1982; 20: 47-55.
20. Tuchscherer G, Servis C, Corradin G, Blum U, Rivier J, Mutter M. Total chemical synthesis, characterization, and immunological properties of an MHC class I model using the TASP concept for protein de novo design. Protein Sci. 1992; 1: 1377-1386.
21. Tan YY, Wade JD, Tregear GW, Summers RJ. Quantitative autoradiographic studies of relaxin binding in rat atria, uterus and cerebral cortex: characterization and effects of oestrogen treatment. Brit. J. Pharmacol. 1999; 127: 91-98.