Transition state structure for the hydrolysis of NAD+ catalyzed by diphtheria toxin

Journal of the American Chemical Society

Volumn 119, Issue 50, 1997, Pages 12079-12088

  Berti, Paul J ^a   Blanke, Steven R ^b,c   Schramm, Vern L ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF HOUSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; DIPHTHERIA TOXIN; ELONGATION FACTOR 2; NICOTINAMIDE ADENINE DINUCLEOTIDE;

ADENOSINE DIPHOSPHATE RIBOSYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CONFORMATIONAL TRANSITION; HYDROLYSIS; NUCLEOTIDE METABOLISM; PROTEIN SYNTHESIS; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0031576682     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971317a     Document Type: Article

References (92)

1. van Geldermalsen, A. A.; Wenning, U. Ann. Trop. Paediatr. 1993, 13, 13-19.
2. Hardy, I. R.; Dittmann, S.; Sutter, R. W. Lancet 1996, 347, 1739-1744.
3. Koo, D.; Traverse, H.; Libel, M.; Drasbek, C.; Tauxe, R.; Brandling-Bennett, D. Bull. Pan Am. Health Org. 1996, 30, 134-143.
4. Swerdlow, D. L.; Levine, O.; Toole, M. J.; Waldman, R. J.; Tauxe, R. V. Lancet 1994, 344, 1302-1303.
5. Siddique, A. K.; Salam, A.; Islam, M. S.; Akram, K.; Majumdar, R. N.; Zaman, K.; Fronczak, N.; Laston, S. Lancet 1995, 345, 359-361.
6. Popovic, T.; Fields, P. I.; Olsvik, O.; Wells, J. G.; Evins, G. M.; Cameron, D. N.; Farmer, J. J. r.; Bopp, C. A.; Wachsmuth, K.; Sack, R. B., et al. J. Infect. Dis. 1995, 171, 122-127.
7. Starke, J. R.; Tan, T. Q.; Chacko, M. R.; Cleary, T. G.; Connelly, K. K.; Kline, M. W. Texas Med. 1994, 90, 35-45.
8. Christie, C. D.; Marx, M. L.; Marchant, C. D.; Reising, S. F. New Engl. J. Med. 1994, 331, 16-21.
9. Rosenthal, S.; Strebel, P.; Cassiday, P.; Sanden, G.; Brusuelas, K.; Wharton, M. J. Infect. Dis. 1995, 171, 1650-1652.
10. De Serres, G.; Boulianne, N.; Douville Fradet, M.; Duval, B. Canada Communicable Dis. Rep. 1995, 21, 45-48.
11. MacIntyre, R.; Hogg, G. Aust. J. Public Health 1994, 18, 21-24.
12. Syedabubakar, S. N.; Matthews, R. C.; Preston, N. W.; Owen, D.; Hillier, V. Epidemiol. Infect. 1995, 115, 101-113.
13. Matter, H. C.; Schmidt-Schlapfer, G.; Zimmermann, H. Schweiz. Med. Wochenschr. 1996, 126, 1423-1432.
14. Montiano Jorge, J. I.; Lazcoz Huarte, A.; Amiama Perez de Villarreal, C.; Mendia Gutierrez, M.; Benito Fernandez, J.; Santiago Burruchaga, M.; Pocheville Guruceta, I.; Gutierrez Villamayor, C.; Gaztelurrutia Abaitua, L. An. Esp. Pediatr. 1992, 37, 184-186.
15. X-Y, bond length between atoms X and Y; SDS-PAGE, sodium dodecyl sulfate polyacrylamide gel electrophoresis; TS, transition state.
16. Wilson, B. A.; Collier, R. J. Curr. Top. Microbiol. Immunol. 1992, 175, 27-41.
17. Li, B. Y. R. S. J. Biol. Chem. 1994, 269, 2652-2658.
18. Murphy, J. R.; vanderSpek, J. C. Sem. Cancer Biol. 1995, 6, 259-267.
19. Kreitman, R. J.; Pastan, I. Sem. Cancer Biol. 1995, 6, 297-306.
20. Roy, D. C.; Ouellet, S.; Le Houillier, C.; Ariniello, P. D.; Perreault, C.; Lambert, J. M. J. Nat. Cancer Inst. 1996, 88, 1136-1145.
21. French, R. R.; Penney, C. A.; Browning, A. C.; Stirpe, F.; George, A. J.; Glennie, M. J. Br. J. Cancer 1995, 71, 986-994.
22. Gould, B. J.; Borowitz, M. J.; Groves, E. S.; Carter, P. W.; Anthony, D.; Weiner, L. M.; Frankel, A. E. J. Nat. Cancer Inst. 1989, 81, 775-781.
23. Pai, L. H.; Pastan, I. In Biologic Therapy of Cancer, 2nd ed.; De Vita, V. T., Jr., Hellman, S., Rosenberg, S. A., Eds.; Lippincott: Philadelphia, PA, 1995; pp 521-533.
24. Sugimura, T.; Miwa, M. Mol. Cell. Biochem. 1994, 138, 5-12.
25. Lee, H. C.; Galione, A.; Walseth, T. F. Vitam. Horm. 1994, 48, 199-257.
26. See: ADP-ribosylation reactions; Poirier, G. G., Moreau, P., Eds.; Springer-Verlag: New York, 1992.
27. Kandel, J.; Collier, R. J.; Chung, D. W. J. Biol. Chem. 1974, 249, 2088-2097.
28. Rising, K. A.; Schramm, V. L. J. Am. Chem. Soc. 1997, 119, 27-37.
29. Scheuring, J.; Schramm, V. L. Biochemistry 1997, 36, 4526-4534.
30. Berti, P. J.; Schramm, V. L. J. Am. Chem. Soc. 1997, 119, 12069-12078.
31. Rising, K. A.; Schramm, V. L. J. Am. Chem. Soc. 1994, 116, 6531-6536.
32. Bennet, A. J.; Sinnott, M. L. J. Am. Chem. Soc. 1986, 108, 7287-7294.
33. Parkin, D. W.; Horenstein, B. A.; Abdulah, D. R.; Estupinan, B.; Schramm, V. L. J. Biol. Chem. 1991, 266, 20658-20665.
34. 18O label in the nicotinamidyl portion, "N".
35. Selwyn, M. J. Biochim. Biophys. Acta 1965, 105, 193-195.
36. Parkin, D. W. In Enzyme mechanism from isotope effects; Cook, P. F., Ed.; CRC Press Inc.: Boca Raton, FL, 1991; pp 269-290.
37. Gawlita, E.; Paneth, P.; Anderson, V. E. Biochemistry 1995, 34, 6050-6058.
38. Bahnson, B. J.; Anderson, V. E. Biochemistry 1991, 30, 5894-5906.
39. Bigeleisen, J.; Wolfsberg, M. Adv. Chem. Phys. 1958, 1, 15-76.
40. Melander, L.; Saunders, W. H., Jr. Reaction rates of isotopic molecules; John Wiley & Sons: New York, 1980; p 98.
41. Sims, L. B.; Burton, G. W.; Lewis, D. E. BEBOVIB-IV, QCPE No. 337; Quantum Chemistry Program Exchange, Department of Chemistry, University of Indiana: Bloomington, IN, 1977.
42. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
43. Perdew, J. P.; Wang, Y. Phys, Rev. B 1992, 45, 13244.
44. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision C.2; Gaussian, Inc.: Pittsburgh, PA, 1995.
45. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
46. Eyster, J. M.; Prohofsky, E. W. Spectrochim. Acta 1974, 30A, 2041-2046.
47. Saunders, M.; Laidig, K. E.; Wolfsberg, M. J. Am. Chem. Soc. 1989, 111, 8989-8994.
48. Blanke, S. R.; Huang, K.; Collier, R. J. Biochemistry 1994, 33, 15494-15500.
49. Rose, I. W. Methods Enzymol. 1980, 64, 47-59.
50. Guthrie, R. D.; Jencks, W. P. Acc. Chem. Res. 1989, 22, 343-349.
51. Northrop, D. B. Annu. Rev. Biochem. 1981, 50, 103-131.
52. Schramm, V. L. In Enzyme mechanism from isotope effects; Cook, P. F., Ed.; CRC Press Inc.: Boca Raton, FL, 1991; pp 367-388.
53. Kline, P. C.; Schramm, V. L. Biochemistry 1995, 34, 1153-1162.
54. Kline, P. C.; Schramm, V. L. Biochemistry 1993, 32, 13212-13219.
55. Horenstein, B. A.; Parkin, D. W.; Estupinan, B.; Schramm, V. L. Biochemistry 1991, 30, 10788-10795.
56. Mentch, F.; Parkin, D. W.; Schramm, V. L. Biochemistry 1987, 26, 921-930.
57. Parkin, D. W.; Schramm, V. L. Biochemistry 1987, 26, 913-920.
58. Parkin, D. W.; Leung, H. B.; Schramm, V. L. J. Biol. Chem. 1984, 259, 9411-9417.
59. Poirier, R. A.; Wang, Y.; Westaway, K. C. J. Am. Chem. Soc. 1994, 116, 2526-2533.
60. Sunko, D. E.; Szele, I.; Hehre, W. J. J. Am. Chem. Soc. 1977, 99, 5000-5004.
61. Ashwell, M.; Guo, X.; Sinnott, M. L. J. Am. Chem. Soc. 1992, 114, 10158-10166.
62. Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
63. Padmaperuma, B.; Sinnott, M. L. Carbohydr. Res. 1993, 250, 79-86.
64. Tull, D.; Withers, S. G. Biochemistry 1994, 33, 6363-6370.
65. Tanaka, Y.; Tao, W.; Blanchard, J. S.; Hehre, E. J. J. Biol. Chem. 1994, 269, 32306-32312.
66. Wang, Q. P.; Graham, R. W.; Trimbur, D.; Warren, R. A. J.; Withers, S. G. J. Am. Chem. Soc. 1994, 116, 11594-11595.
67. Braun, C.; Brayer, G. D.; Withers, S. G. J. Biol. Chem. 1995, 270, 26778-26781.
68. McIntosh, L. P.; Hand, G.; Johnson, P. E.; Joshi, M. D.; Korner, M.; Plesniak, L. A.; Ziser, L.; Wakarchuk, W. W.; Withers, S. G. Biochemistry 1996, 35, 9958-9966.
69. Sinnott, M. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 2026-2032.
70. Kneir, B. L.; Jencks, W. P. J. Am. Chem. Soc. 1980, 102, 6789-6798.
71. Amyes, T. L.; Jencks, W. P. J. Am. Chem. Soc. 1989, 111, 7888-7900.
72. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7951-7958.
73. Banait, N. S.; Jencks, W. P. J. Am. Chem. Soc. 1991, 113, 7958-7963.
74. Cherian, X. M.; Van Arman, S. A.; Czarnick, A. W. J. Am. Chem. Soc. 1990, 112, 4490-4498.
75. Huang, X.; Surry, C.; Hiebert, T.; Bennet, A. J. J. Am. Chem. Soc. 1995, 117, 10614-10621.
76. Westaway, K. C. Tetrahedron Lett. 1975, 48, 4229-4232.
77. Johnson, R. W.; Marschner, T. M.; Oppenheimer, N. J. J. Am. Chem. Soc. 1988, 110, 2257-2263.
78. Choe, S.; Bennett, M. J.; Fujii, G.; Curmi, P. M.; Kantardjieff, K. A.; Collier, R. J.; Eisenberg, D. Nature 1992, 357, 216-222.
79. Bell, C. E.; Eisenberg, D. Biochemistry 1996, 35, 1137-1149.
80. Bell, C. E.; Eisenberg, D. Biochemistry 1997, 36, 481-488.
81. Oppenheimer, N. J.; Bodley, J. W. J. Biol. Chem. 1981, 256, 8579-8581.
82. Carroll, S. F.; McCloskey, J. A.; Crain, P. F.; Oppenheimer, N. J.; Marschner, T. M.; Collier, R. J. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7237-7241.
83. Wilson, B. A.; Reich, K. A.; Weinstein, B. R.; Collier, R. J. Biochemistry 1990, 29, 8643-8651.
84. Desiraju, G. R. Acc. Chem. Res. 1996, 29, 441-449.
85. Desiraju, G. R. Acc. Chem. Res. 1991, 24, 290-296.
86. Horenstein, B. A.; Schramm, V. L. Biochemistry 1993, 32, 7089-7097.
87. Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett. 1993, 34, 7213-7216.
88. Horenstein, B. A.; Schramm, V. L. Biochemistry 1993, 32, 9917-9925.
89. Sims, L. B.; Lewis, D. E. In Isotope effects: Recent developments in theory and experiment; Buncel, E., Lee, C. C., Eds.; Elsevier: New York, 1984; Vol. 6, pp 161-259.
90. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
91. Connolly, M. L. Science 1983, 221, 709-713.
92. Kabsch, W.; Sander, C. Biopolymers 1983, 22, 2577-2637.