D-amino acid residue in a defensin-like peptide from platypus venom: Effect on structure and chromatographic properties

Biochemical Journal

Volumn 391, Issue 2, 2005, Pages 215-220

  Torres, Allan M ^a   Tsampazi, Chryssanthi ^a   Geraghty, Dominic P ^b   Bansal, Paramjit S ^c   Alewood, Paul F ^c   Kuchel, Philip W ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF TASMANIA   (Australia)

^c UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Defensin like peptide (DLP); Nuclear Overhauser spectroscopy; Peptide conformation; Peptide isomerase; Platypus venom peptide

Indexed keywords

BIOCHEMISTRY; CHROMATOGRAPHIC ANALYSIS; CONFORMATIONS; ENZYME KINETICS; ENZYMES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

DEFENSIN-LIKE PEPTIDE (DLP); NUCLEAR OVERHAUSER SPECTROSCOPY; PEPTIDE CONFORMATION; PEPTIDE ISOMERASE; PLATYPUS VENOM PEPTIDE;

AMINO ACIDS;

DEFENSIN; DEXTRO AMINO ACID; ISOMERASE; METHIONINE; NATRIURETIC PEPTIDE TYPE C; VENOM;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; MALE; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PLATYPUS; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN LOCALIZATION; PROTEIN STRUCTURE; PROTEIN TERTIARY STRUCTURE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE ANALYSIS;

AMINO ACID SEQUENCE; AMINO ACIDS; ANIMALS; DEFENSINS; ISOMERASES; ISOMERISM; MALE; MOLECULAR SEQUENCE DATA; PLATYPUS; PROTEIN CONFORMATION; VENOMS;

ANIMALIA; ORNITHORHYNCHUS;

EID: 27444438673     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20050900     Document Type: Article

References (36)

1. Montecucchi, P. C., de Castiglione, R., Piani, S., Gozzini, L. and Erspamer, V. (1981) Amino acid composition and sequence of dermorphin, a novel opiate-like peptide from the skin of Phyllomedusa sauvagei. Int. J. Pept. Protein Res. 17, 275-283
2. Kreil, G. (1997) D-Amino acids in animal peptides. Annu. Rev. Biochem. 66, 337-345
3. Richter, K., Egger, R. and Kreil, G. (1987) D-Alanine in the frog-skin peptide dermorphin is derived from L-alanine in the precursor. Science 238, 200-202
4. Jimenez, E. C., Olivera, B. M., Gray, W. R. and Cruz, L. J. (1996) Contryphan is a D-tryptophan-containing Conus peptide. J. Biol. Chem. 271, 28002-28005
5. Kamatani, Y., Minakata, H., Kenny, P. T., Iwashita, T., Watanabe, K., Funase, K., Sun, X. P., Yongsiri, A., Kim, K. H. and Novales-Li, P. (1989) Achatin-I, an endogenous neuroexcitatory tetrapeptide from Achatina fulica Ferussac containing a D-amino acid residue. Biochem. Biophys. Res. Commun. 160, 1015-1020
6. Ohta, N., Kubota, I., Takao, T., Shimonishi, Y., Yasudakamatani, Y., Minakata, H., Nomoto, K., Muneoka, Y. and Kobayashi, M. (1991) Fulicin, a novel neuropeptide containing a D-amino-acid residue isolated from the ganglia of Achatina fulica. Biochem. Biophys. Res. Commun. 178, 486-493
7. Buczek, O., Yoshikami, D., Bulaj, G., Jimenez, E. C. and Olivera, B. M. (2005) Post-translational amino acid isomerization: a functionally important D-amino acid in an excitatory peptide. J. Biol. Chem. 280, 4247-4253
8. Jacobsen, R., Jimenez, E. C., Grilley, M., Watkins, M., Hillyard, D., Cruz, L. J. and Olivera, B. M. (1998) The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers. J. Pept. Res. 51, 173-179
9. Jacobsen, R. B., Jimenez, E. C., De la Cruz, R. G. C., Gray, W. R., Cruz, L. J. and Olivera, B. M. (1999) A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family. J. Pept. Res. 54, 93-99
10. Soyez, D., Toullec, J. Y., Ollivaux, C. and Geraud, G. (2000) L to D amino acid isomerization in a peptide hormone is a late post-translational event occurring in specialized neurosecretory cells. J. Biol. Chem. 275, 37870-37875
11. Soyez, D., Van Herp, F., Rossier, J., Le Caer, J. P., Tensen, C. P. and Lafont, R. (1994) Evidence for a conformational polymorphism of invertebrate neurohormones: D-amino acid residue in crustacean hyperglycemic peptides. J. Biol. Chem. 269, 18295-18298
12. Gallois, D., Brisorgueil, M. J., Conrath, M., Mailly, P. and Soyez, D. (2003) Posttranslational isomerization of a neuropeptide in crustacean neurosecretory cells studied by ultrastructural immunocytochemistry. Eur. J. Cell Biol. 82, 431-440
13. Yasuda, A., Yasuda, Y., Fujita, T. and Naya, Y. (1994) Characterization of crustacean hyperglycemic hormone from the crayfish (Procambarus clarkii): multiplicity of molecular forms by stereoinversion and diverse functions. Gen. Comp. Endocrinol. 95, 387-398
14. 46 in a calcium channel toxin. Science 266, 1065-1068
15. Shikata, Y., Watanabe, T., Teramoto, T., Inoue, A., Kawakami, Y., Nishizawa, Y., Katayama, K. and Kuwada, M. (1995) Isolation and characterization of a peptide isomerase from funnel web spider venom. J. Biol. Chem. 270, 16719-16723
16. Torres, A. M., Menz, I., Alewood, P. F., Bansal, P., Lahnstein, J., Gallagher, C. H. and Kuchel, P. W. (2002) D-Amino acid residue in the C-type natriuretic peptide from the venom of the mammal, Ornithorhynchus anatinus, the Australian platypus. FEBS Lett. 524, 172-176
17. de Plater, G. M., Martin, R. L. and Milburn, P. J. (1998) A C-type natriuretic peptide from the venom of the platypus (Ornithorhynchus anatinus): structure and pharmacology. Comp. Biochem. Physiol. Part C Pharmacol. Toxicol. Endocrinol. 120, 99-110
18. de Plater, G. M., Martin, R. L. and Milburn, P. J. (1998) The natriuretic peptide (ovCNP-39) from platypus (Ornithorhynchus anatinus) venom relaxes the isolated rat uterus and promotes oedema and mast cell histamine release. Toxicon 36, 847-857
19. Torres, A. M., Alewood, D., Alewood, P. F., Gallagher, C. H. and Kuchel, P. W. (2002) Conformations of platypus venom C-type natriuretic peptide in aqueous solution and sodium dodecyl sulfate. Toxicon 40, 711-719
20. Torres, A. M., Wang, X., Fletcher, J. I., Alewood, D., Alewood, P. F., Smith, R., Simpson, R. J., Nicholson, G. M., Sutherland, S. K., Gallagher, C. H. et al. (1999) Solution structure of a defensin-like peptide from platypus venom. Biochem. J. 341, 785-794
21. Torres, A. M., de Plater, G. M., Doverskog, M., Birinyi-Strachan, L. C., Nicholson, G. M., Gallagher, C. H. and Kuchel, P. W. (2000) Defensin-like peptide-2 from platypus venom: member of a class of peptides with a distinct structural fold. Biochem. J. 348, 649-656
22. Torres, A. M. and Kuchel, P. W. (2004) The β-defensin-fold family of polypeptides. Toxicon 44, 581-588
23. Schnolzer, M., Alewood, P., Jones, A., Alewood, D. and Kent, S. B. (1992) In situ neutralization in Boc-chemistry solid phase peptide synthesis: rapid, high yield assembly of difficult sequences. Int. J. Pept. Protein Res. 40, 180-193
24. Bax, A. and Davis, D. G. (1985) Mlev-17-based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 65, 355-360
25. Kumar, A., Ernst, R. R. and Wüthrich, K. (1980) A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules. Biochem. Biophys. Res. Commun. 95, 1-6
26. 1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun. 113, 967-974
27. Piotto, M., Saudek, V. and Sklenar, V. (1992) Gradient-tailored excitation for single-quantum NMR spectroscopy of aqueous solutions. J. Biomol. NMR 2, 661-665
28. Bartels, C., Xia, T. H., Billeter, M., Guntert, P. and Wüthrich, K. (1995) The program Xeasy for computer-supported NMR spectral-analysis of biological macromolecules. J. Biomol. NMR 6, 1-10
29. Brunger, A. T., Adams, P. D., Clore, G. M., DeLano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J. S., Kuszewski, J., Nilges, M., Pannu, N. S. et al. (1998) Crystallography & NMR system: a new software suite for macromolecular structure determination. Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 905-921
30. Szyperski, T., Guntert, P., Otting, G. and Wüthrich, K. (1992) Determination of scalar coupling-constants by inverse Fourier transformation of in-phase multiplets. J. Magn. Reson. 99, 552-560
31. Mumenthaler, C. and Braun, W. (1995) Automated assignment of simulated and experimental NOESY spectra of proteins by feedback filtering and self-correcting distance geometry. J. Mol. Biol. 254, 465-480
32. Mumenthaler, C., Guntert, P., Braun, W. and Wüthrich, K. (1997) Automated combined assignment of NOESY spectra and three-dimensional protein structure determination. J. Biomol. NMR 10, 351-362
33. Guntert, P., Mumenthaler, C. and Wüthrich, K. (1997) Torsion angle dynamics for NMR structure calculation with the new program DYANA. J. Mol. Biol. 273, 283-298
34. Koradi, R., Billeter, M. and Wüthrich, K. (1996) MOLMOL: a program for display and analysis of macromolecular structures. J. Mol. Graphics 14, 51-55, 29-32
35. Jilek, A., Mollay, C., Tippelt, C., Grassi, J., Mignogna, G., Mullegger, J., Sander, V., Fehrer, C., Barra, D. and Kreil, G. (2005) Biosynthesis of a D-amino acid in peptide linkage by an enzyme from frog skin secretions. Proc. Natl. Acad. Sci. U.S.A. 102, 4235-4239
36. Harada, N., Iijima, S., Kobayashi, K., Yoshida, T., Brown, W. R., Hibi, T., Oshima, A. and Morikawa, M. (1997) Human IgGFc binding protein (FcγBP) in colonic epithelial cells exhibits mucin-like structure. J. Biol. Chem. 272, 15232-15241