Inframolecular protonation process of myo-inositol 1,4,5-tris(phosphate) and related compounds: Dynamics of the intramolecular interactions and evidence of C-H···O hydrogen bonding

Journal of the American Chemical Society

Volumn 122, Issue 13, 2000, Pages 3156-3165

  Felemez, Marc ^a   Bernard, Philippe ^a   Schlewer, Gilbert ^a   Spiess, Bernard ^a  

^a Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYL GROUP; INOSITOL 1,4,5 TRISPHOSPHATE; INOSITOL 1,4,5 TRISPHOSPHATE DERIVATIVE; PHOSPHATE; PHOSPHORUS;

ALKALINITY; ARTICLE; CONFORMATION; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; SOLVATION;

EID: 0034607297     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992940t     Document Type: Article

References (55)

1. Berridge, M. J.; Irvine, R. F. Nature 1984, 312, 315-321.
2. Berridge, M. J. Nature 1993, 361, 315-325.
3. Berridge, M. J.; Bootman, M. D.; Lipp, P. Nature 1998, 395, 645-648.
4. Berridge, M. J. J. Exp. Biol. 1997, 200, 315-319.
5. Berridge, M. J. Ann. N.Y. Acad. Sci. 1996, 31-43.
6. Thomas, A. P.; Bird, G. S. J.; Hajnoczky, G.; Robbgaspers, L. D.; Putney, J. W. FASEB J. 1996, 10, 1505-1517.
7. Wilcox, R. A.; Primrose, W. U.; Nahorski, S. R.; Challiss, R. A. J. Trends Pharmacol. Sci. 1998, 19, 467-475.
8. Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933-1972.
9. Wilcox, R. A.; Fauq, A.; Kozikowski, A. P.; Nahorski, S. R. FEBS Lett. 1997, 402, 241-245.
10. Wilcox, R. A.; Challiss, R. A. J.; Traynor, J. R.; Fauq, A. H.; Ognayanov, V. I.; Kozikowski, A. P.; Nahorski, S. R. J. Biol. Chem. 1994, 209, 26815-26821.
11. Lu, P. J.; Chen, C. S. Phosphorus Sulfur 1996, 110, 325-328.
12. Yoshida, Y.; Imai, S. Jpn. J. Pharmacol. 1997, 74, 125-137.
13. Taylor, C. W.; Traynor, D. J. Membr. Biol. 1995, 145, 109-118.
14. Taylor, C. W. Trends Pharmacol. Sci. 1994, 15, 271-274.
15. Guillemette, G.; Segui, J. A. Mol. Endo. 1988, 2 (12), 1249-1255.
16. O'Rourke, F.; Feinstein, M. B. Biochem. J. 1990, 267, 297-302.
17. Worley, P. F.; Baraban, J. M.; Supattapone, S.; Wilson, V. S.; Snyder, S. H. J. Biol. Chem. 1987, 262, 12132-12136.
18. Schmitt, L.; Schlewer, G.; Spiess, B. Biochim. Biophys. Acta 1991, 1075, 139-140.
19. Guédat, P.; Poitras, M.; Spiess, B.; Guillemette, G.; Schlewer, G. Bioorg. Med. Chem. Lett. 1996, 6, 1175-1178.
20. Isbrandt, L. R.; Oertel, R. P. J. Am. Chem. Soc. 1980, 102, 3144-3148.
21. Brigando, C.; Mossoyan, J. C.; Favier, F.; Benlian, D. J. Chem. Soc., Dalton Trans. 1995, 575-578.
22. Paton, G.; Noailly, M.; Mossoyan, J. C. J. Phys. Org. Chem. 1999, 12, 401-407.
23. Mernissi-Arifi, K.; Schmitt, L.; Schlewer, G.; Spiess, B. Anal. Chem. 1995, 67, 2567-2574.
24. Mernissi-Arifi, K.; Ballereau, S.; Schlewer, G.; Spiess, B.; Zenkouar, M. New J. Chem. 1996, 20, 1087-1092.
25. Guédat, P.; Schlewer, G.; Krempp, E.; Riley, A. M.; Potter, B. V. L.; Spiess, B. Chem. Commun. 1997, 625-626.
26. Riley, A. M.; Guedat, P.; Schlewer, G.; Spiess, B.; Potter, B. V. L. J. Org. Chem. 1998, 63, 295-305.
27. Mernissi-Arifi, K.; Schlewer, G.; Spiess, B. Carbohydr. Res. 1998, 308, 9-17.
28. Schlewer, G.; Guedat, P.; Ballereau, S.; Schmitt, L.; Spiess, B. In Phosphoinositides: chemistry, biochemistry, and biomedical applications; Bruzik, K. S., Ed.; American Chemical Society: Washington, DC, 1999; pp 255-270.
29. Mills, S. J.; Alhafidh, J.; Westwick, J.; Potter, B. V. L. Bioorg. Med. Chem. Lett. 1993, 3, 2599-2604.
30. Poirot, E.; Bourdon, H.; Chretien, F.; Chapleur, Y.; Berthon, B.; Hilly, M.; Mauger, J. P.; Guillon, G. Bioorg. Med. Chem. Lett. 1995, 5, 569-572.
31. Schmitt, L., Bortmann, P.; Schlewer, G.; Spiess, B. J. Chem. Soc., Perkin Trans. 2 1993, 2257-2263.
32. Gans, P.; Sabatini, A.; Vacca, A. J. Chem. Soc., Dalton Trans. 1985, 1195-1200.
33. Frassineti, C.; Ghelli, S.; Gans, P.; Sabatini, A.; Moruzzi, M. S.; Vacca, A. Anal. Biochem. 1995, 231, 374-382.
34. SYBYL Molecular Modeling System (v. 6.5), tripos Associates, St. Louis, MO, 1998.
35. Schweizer, M. P.; Broom, A. D.; Ts'o, P. O. P.; Hollis, D. P. J. Am. Chem. Soc. 1968, 90, 1042-1055.
36. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38.
37. Blindauer, C. A.; Holy, A.; Dvorakova, H.; Sigel, H. J. Chem. Soc., Perkin Trans. 2 1997, 2353-2363.
38. Tribolet, R.; Sigel, H. Eur. J. Biochem. 1987, 163, 353-363.
39. Wang, X.; Simpson, J. H.; Nelson, D. J. J. Inorg. Biochem. 1995, 58, 29-47.
40. Lankhorst, P. P.; Haasnoot, C. A. G.; Erkelens, C.; Altona, C. J. Biomol. Struct. Dyn. 1984, 1, 1387-1405.
41. White, A. M.; Varney, M. A.; Watson, S. P.; Rigby, S.; Changsheng, L.; Ward, J. G.; Reese, C. B.; Graham, H. C.; Williams, R. J. P. Biochem. J. 1991, 278, 759-764.
42. Massoud, S. S.; Sigel, H. Inorg. Chem. 1988, 27, 1447-1453.
43. Cozzone, P. J.; Jardetzky, O. Biochemistry 1976, 15 (22), 4853-4859.
44. Bera, A. K.; Mukhopadhyay, B P.; Pal, A K.; Haldar, U.; Bhattacharya, S.; Banerjee, A. J. Chem. Crystallogr. 1998, 28, 509-516.
45. Jeffrey, G. A. J. Mol. Struct. 1994, 322, 21-25.
46. Auffinger, P.; Louise-May, S.; Westhof, E. Faraday Discuss. 1996, 103, 151-173.
47. Moerdritzer, K. Inorg. Chem. 1967, 6, 936-939.
48. Ollig, J.; Hagele, G. Comput. Chem. 1995, 19, 287-294.
49. Schmitt, L.; Spiess, B.; Schiewer, G. Bioorg. Med. Chem. Lett. 1995, 5, 1225-1230.
50. Lindon, J. C., Baker, D. J.; Farrant, R. D.; Williams, J. M. Biochem. J. 1986, 233, 275-277.
51. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449.
52. Novoa, J. J.; Lafuente, P.; Mota, F. Chem. Phys. Lett. 1998, 519-525.
53. Jeffrey, G. A. J. Mol. Struct. 1999, 485-486, 292-298.
54. Frey, P. A.; Cleland, W. W. Bioorg. Chem. 1998, 26, 175-192.
55. Hirata, M.; Watanabe, Y.; Yoshida, M.; Koga, T.; Ozaki, S. J. Biol. Chem. 1993, 268, 19260-19266.