Synthesis, 1H, 13C, 15N, and 113Cd NMR, ESI-TOF MS, semiempirical MO (PM3), ab initio/HF and cation/anion binding studies of N-deoxycholyl-L-tryptophan

Journal of Inclusion Phenomena

Volumn 43, Issue 3-4, 2002, Pages 319-327

  Virtanen, Elina ^a   Tamminen, Jari ^a   Linnanto, Juha ^a   Mänttäri, Pia ^a   Vainiotalo, Pirjo ^b   Kolehmainen, Erkki ^a  

^a UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Cation anion binding; Deoxycholic acid tryptophan conjugate; ESI TOF MS; MO calculations; Multinuclear magnetic resonance

Indexed keywords

AMINO ACID; BILE ACID; CADMIUM DERIVATIVE; DEOXYCHOLIC ACID; N DEOXYCHOLYLTRYPTOPHAN; NITROGEN; SODIUM; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ACIDITY; ALKALINITY; ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CONFORMATION; EMPIRICISM; ENERGY; HYDROGEN BOND; MASS SPECTROMETRY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PH; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0346394875     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021275012904     Document Type: Article

References (55)

1. A.P. Davis: Chem. Soc. Rev. 22, 243 (1993).
2. U. Maitra: Curr. Sci. 71, 617 (1996).
3. A.P. Davis, R.P. Bonar-Law, and J.K.M. Sanders: Receptors Based on Cholic Acid (Comprehensive Supramolecular Chemistry v. 4, J.L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle eds., Elsevier (1996), p. 257.
4. M. Miyata and K. Sada: Deoxycholic Acid and Related Hosts (Comprehensive Supramolecular Chemistry v. 6, J.L. Atwood, J.E.D. Davies, D.D. MacNicol, and F. Vögtle (eds.)), Elsevier (1996), p. 147.
5. Y. Li and J.R. Dias: Chem. Rev. 97, 283 (1997).
6. P. Wallimann, T. Marti, A. Fürer, and F. Diederich: Chem. Rev. 97, 1567 (1997).
7. A.P. Davis and R.S. Wareham: Angew. Chem., Int. Ed. 38, 2978 (1999).
8. J. Tamminen and E. Kolehmainen: Molecules 6, 21 (2000).
9. A.F. Hofmann: Ital. J. Gastroenterol. 27, 106 (1995).
10. F. Berlati, G. Ceschel, C. Clerici, R. Pellicciari, A. Roda, and C. Ronchi: WO 9,400,126 (1994).
11. B.A. Marples and R.J. Stretton: WO 9,013,298 (1990).
12. A. Enhsen, W. Kramer, and G. Wess: Drug Discovery Today 3, 409 (1998).
13. M.R. Ruff, J.M. Hill, L.D. Kwart, and C.B. Pert: US 5,446,026 (1995).
14. C. Li, A.S. Peters, E.L. Meredith, G.W. Allman, and P.B. Savage: J. Am. Chem. Soc. 120, 2961 (1998).
15. C. Li, L.P. Budge, C.D. Driscoll, B.M. Willardson, G.W. Allman, and P.S. Savage: J. Am. Chem. Soc. 121, 931 (1999).
16. E. Campazzi, M. Cattabriga, L. Marvelli, A. Marchi, R. Rossi, M.R. Pieragnoli, and M. Fogagnolo: Inorg. Chim. Acta 286, 46 (1999).
17. Bondi and Mueller: Z. Physiol. Chem. 47, 499 (1906).
18. F. Cortese and L. Bauman: J. Am. Chem. Soc. 57, 1393 (1935).
19. A. Norman: Ark. Kemi 8, 331 (1955).
20. A.F. Hofmann: Acta. Chem. Scand. 17, 173 (1963).
21. A.M. Ballatore, C.F. Beckner, R.M. Caprioli, N.E. Hoffman, and J.G. Liehr: Steroids 41, 197 (1983).
22. S.M. Huijghebaert and A.F. Hofmann: Gastroenterology 90, 306 (1986).
23. A. Roda, C. Cerrè, A.C. Manetta, G. Cainelli, A. Umani-Ronchi, and M. Panunzio: J. Med. Chem. 39, 2270 (1996).
24. D. Albert and M. Feigel: Tetrahedron Lett. 35, 565 (1994).
25. D. Albert and M. Feigel: Helv. Chim. Acta 80, 2168 (1997).
26. D. Albert, M. Feigel, J. Benet-Buchholtz, and R. Boese: Angew. Chem., Int. Ed. 37, 2727 (1998).
27. K.J. Willis, A.G. Szabo, and D.T. Kracjarski: Chem. Phys. Lett. 182, 614 (1991).
28. X. Cao and G. Fischer: J. Phys. Chem. A 103, 9995 (1999).
29. B. Dezube, C.M. Dobson, and C.F. Teague: J. Chem. Soc., Perkin Trans. 2 730 (1981).
30. K. Aizawa, S. Ohhata, H. Nishie, A. Ohsaka, K. Kato, K. Matsushita, and K. Hioka: Biochem. Biophys. Res. Commun. 146, 791 (1987).
31. S.L. De Wall, E.S. Meadows, L.J. Barbour, and G.W. Gokel: J. Am. Chem. Soc. 121, 5613 (1999).
32. M. Saraswathi and J.M. Miller: Rapid Commun. Mass Spectrom. 10, 1706 (1996).
33. H. Lavanant and Y. Hoppilliard: J. Mass Spectrom. 32, 1037 (1997).
34. C.L. Gatlin and F. Tureček: J. Mass Spectrom. 35, 172 (2000).
35. P.K. Sharma, A.K. Sen, and S.N. Dubey: Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. 33a, 1031 (1994).
36. E. Giglio: Inclusion Compounds (Inclusion Compounds, Vol. 2: Structural Aspect of Inclusion Compounds formed by Organic Hosts Lattices v. 2, J.L. Atwood, J.E.D. Davies, and D.D. MacNicol (eds.)), Academic Press (1984), p. 207.
37. P. Granger: Groups 11 and 12, Copper to Mercury (Transition Metal Nuclear Magnetic Resonance: Studies in Inorganic Chemistry v. 13, P.S. Pregosin (ed.)), Elsevier (1991), p. 293.
38. A.M. Bellini, M.P. Quaglio, M. Guarneri, and G. Cavezzini: Eur. J. Med. Chem.- Chim. Ther. 18, 191 (1983).
39. B. Dayal, J. Bhojawala, K.R. Rapole, B.N. Pramanik, N.H. Ertel, S. Shefer, and G. Salen: Bioorg. Med. Chem. 4, 885 (1996).
40. A. Bax, R.H. Griffey, and B.L. Hawkins: J. Magn. Reson. 55, 301 (1983).
41. A. Bax and S. Subramanian: J. Magn. Reson. 67, 565 (1986).
42. A. Bax and M.F. Summers: J. Am. Chem. Soc. 108, 2093 (1986).
43. M. Rance, O.W. Sørensen, G. Bodenhausen, G. Wagner, R.R. Ernst, and K. Wüthrich: Biochem. Biophys. Res. Commun. 117, 479 (1984).
44. A. Derome and M. Williamson: J. Magn. Reson. 88, 117 (1990).
45. J. Jeener, B.H. Meier, P. Bachmann, and R.R. Ernst: J. Chem. Phys. 69, 4546 (1979).
46. G. Wagner and K. Wüthrich: J. Mol. Biol. 155, 347 (1982).
47. R.E. Hurd and B.K. John: J. Magn. Reson. 91, 648 (1991).
48. J.J.P. Stewart: J. Comp. Chem. 10, 209 (1989).
49. SPARTAN, Version 5.0.2 (Wavefunction Inc., Irvine, CA, 1991-7).
50. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople, GAUSSIAN 98, Revision A.6, Gaussian Inc., Pittsburgh PA, 1998.
51. J.W. Blunt and J.B. Stothers: Org. Magn. Reson. 9, 439 (1977).
52. M.S. Morales-Ríos, J. Espiñeira, and P. Joseph-Nathan: Magn. Reson. Chem. 25, 377 (1987).
53. S. Berger, S. Braun, and H.-O. Kalinowski: NMR Spectroscopy of the Non-Metallic Elements, John Wiley & Sons Ltd. (1997), p. 158.
54. J. Tamminen, E. Kolehmainen, J. Linnanto, P. Vainiotalo, S. Vuorikoski, and R. Kauppinen: J. Incl. Phenom. Macrocycl. Chem. 37, 121 (2000).
55. J.M.J. Nuutinen, M. Purmonen, J. Ratilainen, K. Rissanen, and P. Vainiotalo: Rapid Commun. Mass Spectrom. 15, 1374 (2001).