Side chain contributions to the interconversion of the topological isomers of guanylin-like peptides

Journal of Peptide Science

Volumn 11, Issue 6, 2005, Pages 319-330

  Schulz, Axel ^a   Marx, Ute C ^b   Tidten, Naomi ^b   Lauber, Thomas ^b   Hidaka, Yuji ^c   Adermann, Knut ^a  

^a IPF PHARMACEUTICALS GMBH   (Germany)

^b UNIVERSITY OF BAYREUTH   (Germany)

^c KINKI UNIVERSITY   (Japan)

Author keywords

Guanylin; Interconversion; NMR spectroscopy; Topological isomers; Uroguanylin

Indexed keywords

ALANINE; CHIMERIC PROTEIN; GUANYLIN; UROGUANYLIN;

AMINO ACID ANALYSIS; ARTICLE; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE SYNTHESIS; STEREOSPECIFICITY;

AMINO ACID SEQUENCE; GASTROINTESTINAL HORMONES; INDICATORS AND REAGENTS; ISOMERISM; MOLECULAR SEQUENCE DATA; NATRIURETIC PEPTIDES; OLIGOPEPTIDES; PEPTIDES; SEQUENCE ALIGNMENT; SEQUENCE HOMOLOGY, AMINO ACID;

EID: 20444389029     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/psc.625     Document Type: Article

References (31)

1. Currie MG, Fok KF, Kato J, Moore RJ, Hamra FK, Duffin KL, Smith CE. Guanylin: an endogenous activator of intestinal guanylate cyclase. Proc. Natl Acad. Sci. USA 1992; 89: 947-951.
2. Wiegand RC, Kato J, Huang MD, Fok KF, Kachur JF, Currie MG. Human guanylin: cDNA isolation, structure, and activity. FEBS Lett. 1992; 311: 150-154.
3. Hamra FK, Forte LR, Eber SL, Pidhorodeckyj NV, Krause WJ, Freeman RH, Chin DT, Tompkins JA, Fok KF, Smith CE, Duffin KL, Siegel NR, Currie MG. Uroguanylin: structure and activity of a second endogenous peptide that stimulates intestinal guanylate cyclase. Proc. Natl Acad. Sci. USA 1993; 90: 10 464-10 468.
4. Klodt J, Kuhn M, Marx UC, Martin S, Rösch P, Forssmann WG, Adermann K. Synthesis, biological activity and isomerism of guanylate cyclase C-activating peptides guanylin and uroguanylin. J. Pept. Res. 1997; 50: 222-230.
5. Skelton NJ, Garcia KC, Goeddel DV, Quan C, Burnier JP. Determination of the solution structure of the peptide hormone guanylin: observation of a novel form of topological stereoisomerism. Biochemistry 1994; 33: 13 581-13 592.
6. Marx UC, Klodt J, Meyer M, Gerlach H, Rösch P, Forssmann WG, Adermann K. One peptide, two topologies: structure and interconversion dynamics of human uroguanylin isomers. J. Pept. Res. 1998; 52: 229-240.
7. Schulz A, Escher S, Marx UC, Meyer M, Rösch P, Forssmann WG, Adermann K. Carboxy-terminal extension stabilizes the topological stereoisomers of guanylin. J. Pept. Res. 1998; 52: 518-525.
8. Chino N, Kubo S, Miyazato M, Nakazato M, Kangawa K, Sakakibara S. Generation of two isomers with the same disulfide connectivity during disulfide bond formation of human uroguanylin. Lett. Pept. Sci. 1996; 3: 45-52.
9. Chino N, Kubo S, Kitani T, Yoshida T, Tanabe R, Kobayashi Y, Nakazato M, Kangawa K, Kimura T. Topological isomers of human uroguanylin: interconversion between biologically active and inactive isomers. FEBS Lett. 1998; 421: 27-31.
10. Carpick BW, Gariepy J. The Escherichia coli heat-stable enterotoxin is a long-lived superagonist of guanylin. Infect. Immun. 1993; 61: 4710-4715.
11. Gariepy J, Lane A, Frayman F, Wilbur D, Robien W, Schoolnik GK, Jardetzky O. Structure of the toxic domain of the Escherichia coli heat-stable enterotoxin ST I. Biochemistry 1986; 25: 7854-7866.
12. Field M, Semrad CE. Toxigenic diarrheas, congenital diarrheas, and cystic fibrosis: disorders of intestinal ion transport. Annu. Rev. Physiol. 1993; 55: 631-655.
13. Farthing MJ. Travellers' diarrhoea. Gut 1994; 35: 1-4.
14. Orndorff GR, Sadjimin T, Simanjuntak CH, O'Hanley P, Punjabi NH, Tjokrosonto S, Corwin A, Dibley M, Lebron CI, Echeverria P. Enterotoxigenic Escherichia coli diarrhea in children less than five years of age in central Java. Am. J. Trop. Med. Hyg. 1996; 55: 449-451.
15. Lorenz JN, Nieman M, Sabo J, Sanford LP, Hawkins JA, Elitsur N, Gawenis LR, Clarke LL, Cohen MB. Uroguanylin knockout mice have increased blood pressure and impaired natriuretic response to enteral NaCl load. J. Clin. Invest. 2003; 112: 1244-1254.
16. Min/+ mouse and induces apoptosis in human colon adenocarcinoma cells via cyclic GMP. Cancer Res. 2000; 60: 5151-5157.
17. Favreau P, Krimm I, Le Gall F, Bobenrieth MJ, Lamthanh H, Bouet F, Servent D, Molgo J, Menez A, Letourneux Y, Lancelin JM. Biochemical characterization and nuclear magnetic resonance structure of novel alpha-conotoxins isolated from the venom of Conus consors. Biochemistry 1999; 38: 6317-6326.
18. 1H-NMR spectroscopy and molecular dynamics simulation with the explicit solvent water. Biochim. Biophys. Acta 1997; 1343: 327-334.
19. Nielsen KJ, Watson M, Adams DJ, Hammarstrom AK, Gage PW, Hill JM, Craik DJ, Thomas L, Adams D, Alewood PF, Lewis RJ. Solution structure of μ-conotoxin PIIIA, a preferential inhibitor of persistent tetrodotoxin-sensitive sodium channels. J. Biol. Chem. 2002; 277: 27 247-27 255.
20. Jacobsen RB, Jimenez EC, De la Cruz RGC, Gray WR, Cruz LJ, Olivera BM. A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family. J. Pept. Res. 1999; 54: 93-99.
21. Jacobsen R, Jimenez EC, Grilley M, Watkins M, Hillyard D, Cruz LJ, Olivera BM. The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers. J. Pept. Res. 1998; 51: 173-179.
22. Pallaghy PK, Melnikova AP, Jimenez EC, Olivera BM, Norton RS. Solution structure of contryphan-R, a naturally occurring disulfide-bridged octapeptide containing D-tryptophan: comparison with protein loops. Biochemistry 1999; 38: 11 553-11 559.
23. Pallaghy PK, He W, Jimenez EC, Olivera BM, Norton RS. Structures of the contryphan family of cyclic peptides. Role of electrostatic interactions in cis-trans isomerism. Biochemistry 2000; 39: 12 845-12 852.
24. Hwang TL, Shaka AJ. Water suppression that works. Excitation sculpting using arbitrary wave forms and pulsed field gradients. J. Magn. Reson. 1995; 112: 275-279.
25. Cavannagh J, Rance M. Suppression of cross-relaxation effects on TOCSY spectra via a modified DIPSI-2 mixing sequence. J. Magn. Reson. 1992; 96: 670-678.
26. Friedrich MS. A model-free algorithm for the removal of baseline artifacts. J. Biomol. NMR 1995; 5: 147-153.
27. 1H chemical shifts obtained as a function of temperature and trifluoroethanol concentration for the peptide series GGXGG. J. Biomol. NMR 1995; 5: 14-24.
28. Ozaki H, Sato T, Kubota H, Hata Y, Katsube Y, Shimonishi Y. Molecular structure of the toxin domain of heat-stable enterotoxin produced by a pathogenic strain of Escherichia coli. A putative binding site for a binding protein on rat intestinal epithelial cell membranes. J. Biol. Chem. 1991; 266: 5934-5941.
29. 15N random coli NMR chemical shifts of the common amino acids. I. Investigations of nearest-neighbor effects. J. Biomol. NMR 1995; 5: 67-81.
30. Gray WR, Rivier JE, Galyean R, Cruz LJ, Olivera MM. Conotoxin MI. Disulfide bonding and conformational states. J. Biol. Chem. 1983; 258: 12 247-12 251.
31. Marx UC, Adermann K, Schulz A, Meyer M, Forssmann WG, Rösch P. Structure and function of biological macromolecules. In Dynamics 2001, Jardetzky O, Finucane MD (eds). IOS Press: Amsterdam, 2001; 145-161.