Stacked fluoroaromatics as supramolecular synthons for programming protein dimerization specificity

Angewandte Chemie - International Edition

Volumn 51, Issue 1, 2012, Pages 103-107

  Pace, Christopher J ^a   Zheng, Hong ^a   Mylvaganam, Ruben ^a   Kim, Diane ^a   Gao, Jianmin ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

dipole dipole interactions; protein protein interactions; self assembly; stacking interactions; supramolecular chemistry

Indexed keywords

AROMATIC STACKING INTERACTIONS; DIPOLE DIPOLE INTERACTIONS; DIPOLE-DIPOLE; ENERGETIC FACTORS; PROTEIN DIMERIZATION; PROTEIN MODELS; PROTEIN-PROTEIN INTERACTIONS; SELF-SORTING; STACKING INTERACTION; SUPRAMOLECULAR SYNTHONS; SYSTEMATIC INVESTIGATIONS;

AMINO ACIDS; AROMATIC COMPOUNDS; AROMATIZATION; SUPRAMOLECULAR CHEMISTRY;

PROTEINS;

FLUORINE; PHENYLALANINE; PROTEIN;

ARTICLE; CHEMISTRY; DIMERIZATION; METABOLISM; PROTEIN BINDING; THERMODYNAMICS;

DIMERIZATION; FLUORINE; PHENYLALANINE; PROTEIN BINDING; PROTEINS; THERMODYNAMICS;

EID: 84855260718     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105857     Document Type: Article

References (54)

1. E. Gazit, Chem. Soc. Rev. 2007, 36, 1263-1269
2. E. H. C. Bromley, K. Channon, E. Moutevelis, D. N. Woolfson, ACS Chem. Biol. 2008, 3, 38-50
3. M. C. Branco, J. P. Schneider, Acta Biomater. 2009, 5, 817-831
4. S. Cavalli, F. Albericio, A. Kros, Chem. Soc. Rev. 2010, 39, 241-263
5. H. Robson Marsden, A. Kros, Angew. Chem. 2010, 122, 3050-3068
6. Angew. Chem. Int. Ed. 2010, 49, 2988-3005.
7. S. K. Burley, G. A. Petsko, Science 1985, 229, 23-28
8. G. B. McGaughey, M. Gagne, A. K. Rappé, J. Biol. Chem. 1998, 273, 15458-15463.
9. M. Reches, E. Gazit, Science 2003, 300, 625-627
10. M. G. Woll, E. B. Hadley, S. Mecozzi, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 15932-15933
11. D. M. Ryan, T. M. Doran, B. L. Nilsson, Langmuir 2011, 27, 11145-11156.
12. C. A. Hunter, Angew. Chem. 1993, 105, 1653-1655
13. Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586
14. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244
15. Angew. Chem. Int. Ed. 2003, 42, 1210
16. R. M. Johnson, K. Hecht, C. M. Deber, Biochemistry 2007, 46, 9208-9214
17. M. L. Waters, Curr. Opin. Chem. Biol. 2002, 6, 736-741
18. S. L. Cockroft, C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Am. Chem. Soc. 2005, 127, 8594-8595.
19. D. A. Dougherty, Science 1996, 271, 163-168
20. S. Mecozzi, A. P. West, Jr., D. A. Dougherty, Proc. Natl. Acad. Sci. USA 1996, 93, 10566-10571
21. J. P. Gallivan, D. A. Dougherty, J. Am. Chem. Soc. 2000, 122, 870-874
22. Y. Mo, G. Subramanian, J. Gao, D. M. Ferguson, J. Am. Chem. Soc. 2002, 124, 4832-4837
23. R. M. Hughes, K. R. Wiggins, S. Khorasanizadeh, M. L. Waters, Proc. Natl. Acad. Sci. USA 2007, 104, 11184-11188.
24. C. R. Patrick, G. S. Prosser, Nature 1960, 187, 1021
25. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525-5534
26. J. H. Williams, J. K. Cockcroft, A. N. Fitch, Angew. Chem. 1992, 104, 1666-1669
27. Angew. Chem. Int. Ed. Engl. 1992, 31, 1655-1657
28. J. H. Williams, Acc. Chem. Res. 1993, 26, 593-598
29. F. Cozzi, F. Ponzini, R. Annunziata, M. Cinquini, J. S. Siegel, Angew. Chem. 1995, 107, 1092-1094
30. Angew. Chem. Int. Ed. Engl. 1995, 34, 1019-1020
31. R. E. Gillard, J. F. Stoddart, A. J. P. White, B. J. Williams, D. J. Williams, J. Org. Chem. 1996, 61, 4504-4505
32. A. P. West, Jr., S. Mecozzi, D. A. Dougherty, J. Phys. Org. Chem. 1997, 10, 347-350
33. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290-293
34. Angew. Chem. Int. Ed. Engl. 1997, 36, 248-251
35. S. M. Butterfield, P. R. Patel, M. L. Waters, J. Am. Chem. Soc. 2002, 124, 9751-9755.
36. H. Zheng, J. Gao, Angew. Chem. 2010, 122, 8817-8821
37. Angew. Chem. Int. Ed. 2010, 49, 8635-8639
38. H. Robson Marsden, J. G. Fraaije, A. Kros, Angew. Chem. 2010, 122, 8750-8752
39. Angew. Chem. Int. Ed. 2010, 49, 8570-8572.
40. R. B. Hill, W. F. DeGrado, J. Am. Chem. Soc. 1998, 120, 1138-1145.
41. D. P. Raleigh, S. F. Betz, W. F. DeGrado, J. Am. Chem. Soc. 1995, 117, 7558-7559.
42. L. M. Salonen, M. Ellermann, F. Diederich, Angew. Chem. 2011, 123, 4908-4944
43. Angew. Chem. Int. Ed. 2011, 50, 4808-4842.
44. H. Zheng, K. Comeforo, J. Gao, J. Am. Chem. Soc. 2009, 131, 18-19.
45. E. N. G. Marsh, Chem. Biol. 2000, 7, 153-157
46. N. C. Yoder, K. Kumar, Chem. Soc. Rev. 2002, 31, 335-341.
47. J. S. Lai, J. Qu, E. T. Kool, Angew. Chem. 2003, 115, 6155-6159
48. Angew. Chem. Int. Ed. 2003, 42, 5973-5977
49. Y. Benitex, A. M. Baranger, J. Am. Chem. Soc. 2011, 133, 3687-3689.
50. S. E. Wheeler, J. Am. Chem. Soc. 2011, 133, 10262-10274.
51. C. Y. Kim, J. S. Chang, J. B. Doyon, T. T. Baird, C. A. Fierke, A. Jain, D. W. Christianson, J. Am. Chem. Soc. 2000, 122, 12125-12134
52. C. Y. Kim, P. P. Chandra, A. Jain, D. W. Christianson, J. Am. Chem. Soc. 2001, 123, 9620-9627
53. J. B. Doyon, E. A. Hansen, C. Y. Kim, J. S. Chang, D. W. Christianson, R. D. Madder, J. G. Voet, T. A. Baird, C. A. Fierke, A. Jain, Org. Lett. 2000, 2, 1189-1192
54. A. X. Zhang, R. P. Murelli, C. Barinka, J. Michel, A. Cocleaza, W. L. Jorgensen, J. Lubkowski, D. A. Spiegel, J. Am. Chem. Soc. 2010, 132, 12711-12716.