X-ray and Nuclear Magnetic Resonance (NMR) Studies of Signalizing the Tripeptide Sequence (Tyr-D-Ala-Phe) of Dermorphin and Deltorphins I and II. Comparative Analysis in the Liquid and Solid Phases

Journal of Physical Chemistry B

Volumn 108, Issue 14, 2004, Pages 4535-4545

  Słabicki, Mikołaj M ^a,b   Potrzebowski, Marek J ^a   Bujacz, Grzegorz ^b   Olejniczak, Sebastian ^a   Olczak, Jacek ^c  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^c TriMen Chemicals Ltd   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; CONFORMATIONS; CRYSTAL STRUCTURE; ISOMERS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROBABILITY DENSITY FUNCTION; TENSORS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION ANALYSIS;

CHEMICAL SHIFTS; CROSS-POLARIZATION (CP); DENSITY FUNCTION THEORY (DFT);

POLYPEPTIDES;

EID: 2342421886     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0372690     Document Type: Article

References (60)

1. (a) Okada, Y.; Tsuda, Y.; Bryant, S. D.; Lazarus, L. H. Vitam. Horm. (San Diego) 2002, 65, 257.
2. (b) Pogozheva, I. D.; Lomize, A. L.; Mosberg, H. I. Biophys. J. 1998, 75, 612.
3. (c) Smith, A. P.; Lee, N. M. Life Sci. 2003, 73, 1873.
4. Snyder, S. H.; Pasternak, G. W. Trends Phamacol. Sci. 2003, 24, 198.
5. Deschamps, J. R.; George, C.; Flippen-Anderson, J. L. Biopolymers 1996, 40, 121.
6. Hruby, V. J.; Agnes, R. S. Biopolymers 1999, 51, 391.
7. Daly, J. W.; Caceres, J.; Moni, R. W.; Gusovky, F.; Moos, M.; Seamon, K. B.; Milton, K.; Myers, C. W. Pharmacology 1992, 89, 10960.
8. Montecucchi, P. C.; de Castiglione, R.; Piani, S.; Gozzini, L.; Erspamer, V. Int. J. Pept. Protein Res. 1981, 17, 275.
9. Erspamer, V. Int. J. Dev. Neurosci. 1992, 10, 3.
10. Hong, J.; Rhoheng, Z.; Xiaoyu, H.; Luhua, L.; Xiaojie, X. Biochem. Biophys. Res. Commun. 1995, 207, 99.
11. Mignogna, G.; Severini, C.; Simmaco, M.; Negri, L.; Erspamer, G. F.; Kreil, G.; Barra, D. FEBS Lett. 1992, 302, 151.
12. Temussi, P. A.; Picone, D.; Tanored, T.; Tomatis, R.; Salvadori, S.; Marastoni, M.; Balboni, G. FEES Lett. 1989, 247, 283.
13. Tancredi, T.; Temussi, P. A.; Picone, D.; Amodeo, P.; Tomatis, R.; Salvadori, S.; Marastioni, M.; Santaga, V.; Balboni, G. Biopolymers 1991, 31, 751.
14. Tourwe, D.; Verschueren, K.; Frycia, A.; Davis, P.; Porreca, F.; Hruby, V. J.; Toth, G.; Jaspers, H.; Verheyden, P.; Van Binst, G. Biopolymers 1996, 38, 1.
15. (a) Castiglione-Morelli, M. A.; Lelj, F.; Pastore, A.; Salvadori, S.; Tancredi, T.; Tomatis, R.; Trivellone, E.; Temussi, P. A. J. Med. Chem. 1987, 30, 2067.
16. (b) Nikiforovich, G. V.; Hruby, V. J.; Prakash, O.; Gehrig, A. Biopolymers 1991, 31, 941.
17. (c) Segawa, M.; Ohno, Y.; Doi, M.; Ishida, T.; Iwashita, T. Int. J. Peptide Res. 1995, 46, 37.
18. Sheldrick, G. M.; Kruger, G. M.; Goddard, R. SHELXS-86. Structure Solution Program. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, A46, 467-473.
19. Sheldrick, G. M. SHELXL-93, Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1993.
20. Morcombe, C. R.; Zilm, K. W. J. Magn. Reson. 2003, 162, 479.
21. Win-NMR, Version 6.0; Bruker-Franzen Analytik GmbH: Bremen, Germany, 1993.
22. Antzutkin, O. N.; Shekar, S. C.; Levitt, M. H. J. Magn. Reson. 1995, 115, 7.
23. Bak, M.; Rasmussen, J. T.; Nielsen, N. C. J. Magn. Reson. 2000, 147, 296.
24. Frisch, M. J,; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuok, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
25. Canet, D.; Brondeau, J.; Elbayed, K. J. Magn. Reson. 1988, 77, 483.
26. Torchia, D. A. J. Magn. Reson. 1978, 30, 613.
27. Tooyama, I.; Abe, H.; Renda, T. G. Peptides 2000, 21, 1649.
28. Brandi, M.; Weiss, M. S.; Jabs, A.; Suhnel, J.; Hilgenfeld, R. J. Mol. Biol. 2001, 16, 307, 357.
29. Metz, G.; Wu, X.; Smith, S. O. J. Magn. Reson., Ser. A 1994, 110, 219.
30. Bennett, A. W.; Rienstra, C. M.; Auger, M.; Lakshmi, K. V.; Griffin, R. G. J. Chem. Phys. 1995, 16, 103.
31. (a) Hu, J.; Wang, W.; Liu, F.; Solum, M. S.; Alderman, D. W.; Pugmire, R. J. J. Magn. Reson., Ser. A 1995, 113, 210.
32. (b) Alderman, D. W.; McGeorge, G.; Hu, J. Z.; Pugmire, R. J.; Grant, D. M. Mol. Phys. 1998, 95, 1113.
33. (c) Frydman, L.; Chingas, G. C.; Lee, Y. K.; Grandinetti, P. J.; Eastman, M. A.; Barrai, G. A.; Pines, A. J. Chem. Phys. 1992, 97, 480.
34. (d) Kolbert, A. C.; Griffin, R. G. Chem. Phys. Lett. 1990, 166, 87.
35. Antzutkin, O. N. Prog. NMR Spectrosc. 1999, 35, 203.
36. Dixon, W. T. J. Chem. Phys. 1982, 77, 1800.
37. Ye, C.; Fu, R.; Hu, J.; Hou, L.; Ding, S. Magn. Reson. Chem. 1993, 31, 699.
38. Gu, Z. T.; McDermott, A. J. Am. Chem. Soc. 1993, 115, 4282.
39. Gu, Z. T.; Zambrano, R.; McDermott, A. J. Am. Chem. Soc. 1994, 116, 6368.
40. Ando, I.; Kuroki, S.; Kurosu, H.; Yamanobe, T. Prog. Nucl. Magn. Reson. Spectrosc. 2001, 39, 79 and references therein.
41. (a) Oldfield, E. Annu. Rev. Phys. Chem. 2002, 53, 349 and references therein.
42. (b) Wei, Y.; Lee, D. K.; Ramamoorthy, A. J. Am. Chem. Soc. 2001, 123, 6118.
43. (a) Grant, D. M.; Facelli, J. C.; Alderman, D. W.; Sherwood, M. H. In Nuclear Magnetic Shielding and Molecular Structure; Tossell, J. A., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1993; p 367.
44. (b) Malkin, V. G.; Malkina, O. L.; Eriksson, L. A.; Salahub, D. R. Modern Density Functional Theory: A Tool for Chemistry. In Theoretical and Computational Chemistry, Vol. 2; Serminaro, J. M., Politzer, P., Eds.; Elsevier, Amsterdam, 1995.
45. Inglefield, P. T.; Amicim, R. M.; O'Gara, J. F.; Hung, C.-C.; Jones, A. A. Macromolecules 1983, 16, 1552.
46. (a) Gall, C. M.; Diverdi, J. A.; Opella, S. J. J. Am. Chem. Soc. 1981, 103, 5039.
47. (b) Kinsey, R. A.; Kintanar, A.; Tsai, M. D.; Smith, R. L.; Janes, N.; Oldfield, E. J. Biol. Chem. 1981, 256, 4146.
48. (c) Hiyama, Y.; Silverton, J. V.; Torchia, D. A.; Gerig, J. T.; Hammond, S. J. J. Am. Chem. Soc. 1986, 108, 2715.
49. Kolodziejski, W.; Klinowski, J. Chem. Rev. 2002, 102, 613.
50. Straus, S. K.; Bremi, T.; Evnat, R. R. J. Biomol. NMR 1997, 10, 119.
51. (a) Alla, M.; Lippmaa, E. Chem. Phys. Lett. 1976, 37, 260.
52. (b) Opella, S. J.; Frey, M. H. J. Am. Chem. Soc. 1979, 37, 260.
53. (c) Zilm, K. W. In Spectral Editing Techniques: Hydrocarbon Solids; Grant, D. M., Harris, R. K., Eds.; Encyclopedia of Nuclear Magnetic Resonance, Vol. VII; Wiley: Chichester, U.K., 1996; 4498 pp.
54. Beshah, K.; Olejniczak, E. T.; Griffin, R. G. J. Chem. Phys. 1987, 86, 4730.
55. Lyerla, J. R. High-Resolution NMR of Glassy Amorphous Polymers (Chapter 3). In High-Resolution NMR Spectroscopy of Synthetic Polymers in Bulk; Komorowski, R. A., Ed.; VCH Publishers: Deerfield Beach, FL, 1986; pp 63-119.
56. de Dios, A. C.; Laws, D. D.; Oldfield, E. J. Am. Chem. Soc. 1994, 116, 7784.
57. (a) Kamihira, M.; Naito, A.; Tuzi, S.; Saito, H. J. Phys. Chem. A 1999, 103, 3356.
58. (b) Kamihira, M.; Naito, A,; Nishimura, K.; Tuzi, S.; Saito, H. J. Phys. Chem. B 1998, 102, 2826.
59. Werbelow, L. O.; Chenon, T. M. J. Am. Chem. Soc. 2002, 124, 14066.
60. Data from the Cambridge Crystallographic Data Centre is available free of charge via the Internet, at www.ccdc.cam.ac.uk/-const/retrieving.html, as well as via E-mail (deposit@ccdc.cam.ac.uk), postal service (Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, U.K.), or fax (+44-1223/336-033).