Structure of indole⋯imidazole heterodimer in a supersonic jet: A gas phase study on the interaction between the aromatic side chains of tryptophan and histidine residues in proteins

Journal of Physical Chemistry A

Volumn 116, Issue 47, 2012, Pages 11573-11580

  Kumar, Sumit ^a   Mukherjee, Ankita ^a   Das, Aloke ^a  

^a INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SIDE CHAINS; BINDING MOTIF; DIFFERENT STRUCTURE; GASPHASE; HETERODIMERS; HISTIDINE RESIDUES; HOLE BURNING; HOLE BURNING SPECTROSCOPY; IR SPECTRUM; MOLECULAR LEVELS; NON-COVALENT INTERACTION; QUANTUM CHEMISTRY CALCULATIONS; SPECTROSCOPIC INVESTIGATIONS; SPECTROSCOPIC TECHNIQUE; STACKING INTERACTION; SUPERSONIC JETS; TWO PHOTON IONIZATION; V-SHAPED STRUCTURE;

AMINO ACIDS; AROMATIC COMPOUNDS; BIOMOLECULES; CHROMOPHORES; EXPERIMENTS; HYDROGEN BONDS; PROTEINS; QUANTUM CHEMISTRY; SUPERSONIC AERODYNAMICS;

DIMERS;

FLAVOPROTEIN; HISTIDINE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; TRYPTOPHAN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DIMERIZATION; GAS; HYDROGEN BOND; STATIC ELECTRICITY; VIBRATION;

DIMERIZATION; FLAVOPROTEINS; GASES; HISTIDINE; HYDROGEN BONDING; IMIDAZOLES; INDOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STATIC ELECTRICITY; TRYPTOPHAN; VIBRATION;

EID: 84870428917     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp309167a     Document Type: Article

References (76)

1. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250
2. Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28
3. Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995-8001
4. Bhattacharyya, R.; Samanta, U.; Chakrabarti, P. Protein Eng. 2002, 15, 91-100
5. Samanta, U.; Pal, D.; Chakrabarti, P. Acta Crystallogr., Sect. D 1999, 55, 1421-1427
6. Burley, S. K.; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189
7. Aravinda, S.; Shamala, N.; Das, C.; Sriranjini, A.; Karle, I. L.; Balaram, P. J. Am. Chem. Soc. 2003, 125, 5308-5315
8. Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885-894
9. Alagona, G.; Ghio, C.; Monti, S. J. Phys. Chem. A 1998, 102, 6152-6160
10. Cauët, E.; Rooman, M.; Wintjens, R.; Liévin, J.; Biot, C. J. Chem. Theory Comput. 2005, 1, 472-483
11. Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 4808-4842
12. Lanzarotti, E.; Biekofsky, R. R.; Estrin, D. o. A.; Marti, M. A.; Turjanski, A. n. G. J. Chem. Inf. Model. 2011, 51, 1623-1633
13. Fernández-Recio, J.; Vázquez, A.; Civera, C.; Sevilla, P.; Sancho, J. J. Mol. Biol. 1997, 267, 184-197
14. Weigt, M.; White, R. A.; Szurmant, H.; Hoch, J. A.; Hwa, T. Proc. Natl. Acad. Sci. 2009, 106, 67-72
15. Moore, S. A.; James, M. N. G. J. Mol. Biol. 1995, 249, 195-214
16. Gervasio, F. L.; Procacci, P.; Cardini, G.; Guarna, A.; Giolitti, A.; Schettino, V. J. Phys. Chem. B 2000, 104, 1108-1114
17. Chelli, R.; Gervasio, F. L.; Procacci, P.; Schettino, V. J. Am. Chem. Soc. 2002, 124, 6133-6143
18. Alagona, G.; Ghio, C.; Giolitti, A.; Monti, S. Theor. Chem. Acc. 1999, 101, 143-150
19. Serrano, L.; Bycroft, M.; Fersht, A. R. J. Mol. Biol. 1991, 218, 465-475
20. Espinoza-Fonseca, L. M.; García-Machorro, J. Biochem. Biophys. Res. Commun. 2008, 370, 547-551
21. Singh, J.; Thornton, J. M. FEBS Lett. 1985, 191, 1-6
22. Kannan, N.; Vishveshwara, S. Protein Eng. 2000, 13, 753-761
23. Desiraju, G. R.; Steiner, T. The Weak Hydrogen Bond in Structural Chemistry and Biology; Oxford University Press: New York, 1999.
24. Williams, S.; Bledsoe, R. K.; Collins, J. L.; Boggs, S.; Lambert, M. H.; Miller, A. B.; Moore, J.; McKee, D. D.; Moore, L.; Nichols, J.; Parks, D.; Watson, M.; Wisely, B.; Willson, T. M. J. Biol. Chem. 2003, 278, 27138-27143
25. Henson, B. F.; Hartland, G. V.; Venturo, V. A.; Hertz, R. A.; Felker, P. M. Chem. Phys. Lett. 1991, 176, 91-98
26. Arunan, E.; Gutowsky, H. S. J. Chem. Phys. 1993, 98, 4294-4296
27. Henson, B. F.; Hartland, G. V.; Venturo, V. A.; Felker, P. M. J. Chem. Phys. 1992, 97, 2189-2208
28. Hobza, P.; Selzle, H. L.; Schlag, E. W. J. Am. Chem. Soc. 1994, 116, 3500-3506
29. Janowski, T.; Pulay, P. Chem. Phys. Lett. 2007, 447, 27-32
30. Erlekam, U.; Frankowski, M.; von Helden, G.; Meijer, G. Phys. Chem. Chem. Phys. 2007, 9, 3786-3789
31. Erlekam, U.; Frankowski, M.; Meijer, G.; von Helden, G. J. Chem. Phys. 2006, 124, 171101-171104
32. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2001, 124, 104-112
33. DiStasio, R. A., Jr.; von Helden, G.; Steele, R. P.; Head-Gordon, M. Chem. Phys. Lett. 2007, 437, 277-283
34. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. J. Am. Chem. Soc. 2002, 124, 10887-10893
35. Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2006, 110, 10656-10668
36. Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2004, 108, 10200-10207
37. Varshey, D. B.; Sander, J. R. G.; Frişçić, T.; MacGillivray, L. R. In Supramolecular Chemistry; John Wiley & Sons, Ltd.: New York, 2012.
38. Tiekink, E. R. T.; Zukerman-Schpector, J. The Importance of φ-Interactions in Crystal Engineering: Frontiers in Crystal Engineering; John Wiley and Sons: New York, 2012.
39. Desiraju, G. R. Angew. Chem., Int. Ed. 2007, 46, 8342-8356
40. Desiraju, G. R. Angew. Chem., Int. Ed. 1995, 34, 2311-2327
41. Lehn, J.-M. Supramolecular Chemistry: Concepts and Perspectives; John Wiley & Sons: New York, 1996.
42. Gerhards, M.; Unterberg, C.; Gerlach, A.; Jansen, A. Phys. Chem. Chem. Phys. 2004, 6, 2682-2690
43. Gerhards, M.; Unterberg, C. Phys. Chem. Chem. Phys. 2002, 4, 1760-1765
44. Ebata, T.; Watanabe, T.; Mikami, N. J. Phys. Chem. 1995, 99, 5761-5764
45. Hobza, P.; Riehn, C.; Weichert, A.; Brutschy, B. Chem. Phys. 2002, 283, 331-339
46. Brause, R.; Santa, M.; Schmitt, M.; Kleinermanns, K. ChemPhysChem 2007, 8, 1394-1401
47. Kolaski, M.; Kumar, A.; Singh, N. J.; Kim, K. S. Phys. Chem. Chem. Phys. 2011, 13, 991-1001
48. Weichert, A.; Riehn, C.; Brutschy, B. J. Phys. Chem. A 2001, 105, 5679-5691
49. Connell, L. L.; Ohline, S. M.; Joireman, P. W.; Corcoran, T. C.; Felker, P. M. J. Chem. Phys. 1992, 96, 2585-2593
50. Schmitt, M.; Henrichs, U.; Muller, H.; Kleinermanns, K. J. Chem. Phys. 1995, 103, 9918-9928
51. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 289-300
52. Koláŗ, M.; Hobza, P. J. Phys. Chem. A 2007, 111, 5851-5854
53. Braun, J.; Neusser, H. J.; Hobza, P. J. Phys. Chem. A 2003, 107, 3918-3924
54. Braun, J. E.; Grebner; Neusser, H. J. J. Phys. Chem. A 1998, 102, 3273-3278
55. Geng, Y.; Takatani, T.; Hohenstein, E. G.; Sherrill, C. D. J. Phys. Chem. A 2010, 114, 3576-3582
56. Biswal, H. S.; Gloaguen, E.; Mons, M.; Bhattacharyya, S.; Shirhatti, P. R.; Wategaonkar, S. J. Phys. Chem. A 2011, 115, 9485-9492
57. Soares, A. M.; Giglio, J. R. Toxicon 2003, 42, 855-868
58. Whitaker, R. D.; Cho, Y.; Cha, J.; Carrell, H. L.; Glusker, J. P.; Karplus, P. A.; Batt, C. A. J. Biol. Chem. 1995, 270, 22895-22906
59. Lewendon, A.; Murray, I. A.; Shaw, W. V.; Gibbs, M. R.; Leslie, A. G. W. Biochemistry 1994, 33, 1944-1950
60. Fuhrmann, C. N.; Kelch, B. A.; Ota, N.; Agard, D. A. J. Mol. Biol. 2004, 338, 999-1013
61. Buckle, A. M.; Fersht, A. R. Biochemistry 1994, 33, 1644-1653
62. Kumar, S.; Biswas, P.; Kaul, I.; Das, A. J. Phys. Chem. A 2011, 115, 7461
63. Jurecka, P.; Sponer, J.; Cerny, J.; Hobza, P. Phys. Chem. Chem. Phys. 2006, 8, 1985-1993
64. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566
65. Frisch, M. J. GAUSSIAN 09, Revision B.01; Gaussian, Inc., Wallingford CT, 2009.
66. Su, P.; Li, H. J. Chem. Phys. 2009, 131, 14102-14115
67. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347-1363
68. Hager, J. W.; Demmer, D. R.; Wallace, S. C. J. Phys. Chem. 1987, 91, 1375-1382
69. Carney, J. R.; Hagemeister, F. C.; Zwier, T. S. J. Chem. Phys. 1998, 108, 3379-3382
70. Zischang, J.; Lee, J. J.; Suhm, M. A. J. Chem. Phys. 2011, 135, 061102-061104
71. Choi, M. Y.; Miller, R. E. J. Phys. Chem. A 2006, 110, 9344-9351
72. Kumar, S.; Kaul, I.; Biswas, P.; Das, A. J. Phys. Chem. A 2011, 115, 10299-10308
73. Wassermann, T. N.; Rice, C. A.; Suhm, M. A.; Luckhaus, D. J. Chem. Phys. 2007, 127, 234309-234309
74. Matsumoto, Y.; Honma, K. J. Chem. Phys. 2007, 127, 184310-184319
75. Dauster, I.; Rice, C. A.; Zielke, P.; Suhm, M. A. Phys. Chem. Chem. Phys. 2008, 10, 2827-2835
76. Pfaffen, C.; Infanger, D.; Ottiger, P.; Frey, H.-M.; Leutwyler, S. Phys. Chem. Chem. Phys. 2011, 13, 14110-14118