Creation and investigation of protein-core mimetics with parallel and antiparallel aligned amino acids

Journal of Organic Chemistry

Volumn 70, Issue 11, 2005, Pages 4452-4459

  Fotins, Juris ^a   Smithrud, David B ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CONFORMATIONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HALOGEN COMPOUNDS; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROSCOPIC ANALYSIS;

CHLOROFORM; MIMETIC PROTEIN CORES; SPATIAL ARRANGEMENT;

PROTEINS;

AMINO ACID DERIVATIVE; AROMATIC COMPOUND; AROMATIC NITRO COMPOUND; CHLOROFORM; LEUCINE; PHENYLALANINE; PROTEIN;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR MODEL; PARALLEL DESIGN; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT;

AMINO ACIDS; HYDROGEN BONDING; LEUCINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PHENYLALANINE; PROTEIN CONFORMATION; PROTEINS; THERMODYNAMICS;

EID: 19544363410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479563     Document Type: Article

References (63)

1. (a) Cheng R. P. Curr. Opin. Struct. Biol. 2004, 14, 512-520.
2. (b) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
3. (c) Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650-653.
4. (d) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
5. (a) Blomberg, D.; Hedenstrom, M.; Kreye, P.; Sethson. I.; Brickmann, K.; Kihlberg, J. J. Org. Chem. 2004, 69, 3500-3508.
6. (b) Tatko, C. D.; Waters, M. L. J. Am. Chem. Soc. 2004, 126, 2028-2034.
7. (c) Nowick, J. S.; Brower, J. O. J. Am. Chem. Soc. 2003, 125, 876-877.
8. (d) Nowick, J. S.; Lam, K. S.; Khasanova, T. V.; Kemnitzer, W. E.; Maitra, S.; Mee, H. T.; Liu, R. W. J. Am. Chem. Soc. 2002, 124, 4972-4973.
9. (e) Kaul, R.; Deechongkit, S.; Kelly, J. W. J. Am. Chem. Soc. 2002, 124, 11900-11907.
10. (f) Wang, W.; Yang, J.; Ying, J.; Xiong, C.; Zhang, J.; Cai, C.; Hruby, V. J. J. Org. Chem. 2002, 67, 6353-6360.
11. (g) Fernandez, M. M.; Diez, A.; Rubiralta, M.; Montenegro, E.; Casamitjana, N.; Kogan, M. J.; Giralt, E. J. Org. Chem. 2002, 67, 7587-7599.
12. (h) Eguchi, M.; Shen, R. Y. W.; Shea, J. P.; Lee, M. S.; Kahn, M. J. Med. Chem. 2002, 45, 1395-1398.
13. (i) Hoffmann, T.; Lanig, H.; Waibel, R.; Gmeiner, P. Angew. Chem., Int. Ed. 2001, 40, 3361-3364.
14. (j) Lacroix, E.; Kortemme, T.; de la Paz, M. L.; Serrano, L. Curr. Opin. Struct. Biol. 1999, 9, 487-493.
15. (k) Blanco, F.; Ramírez-Alvarado; M.; Serrano, L. Curr. Opin. Struct. Biol. 1998, 8, 107-111.
16. (l) Gellman, S. H. Curr. Opin. Chem. Biol. 1998, 2, 717-725.
17. (m) Smith, C. K.; Regan, L. Acc. Chem. Res. 1997, 30, 153-161.
18. Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988-4005.
19. Desiraju, G. R.; Gavezzotti, A. J. Chem. Soc., Chem. Commun. 1989, 621-623.
20. (a) Thomas, A.; Meurisse, R.; Charloteaux, B.; Brasseur, R. Proteins 2002, 48, 628-634.
21. (b) Thomas, A.; Meurisse, R.; Brasseur, R. Proteins 2002, 48, 635-644.
22. (c) McGaughey. G. B.; Gagne, M.; Rappe, A. K. J. Biol. Chem. 1998, 273, 15458-15463.
23. (d) Hunter, C. A.; Singh, J.; Thornton, J. M. J. Mol. Biol. 1991, 218, 837.
24. (e) Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986, 108, 7995-8001.
25. (g) Burley, S. K; Petsko, G. A. Science 1985, 229, 23-28.
26. (a) Waters, M. L. Biopolymers 2004, 76, 435-445.
27. (b) Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
28. (c) Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736-741.
29. (d) Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860-1861.
30. (e) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
31. (f) Carver, F. J.; Hunter, C. A.; Jones, P. S.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M.; Tiger, P.; Spey, S. E. Chem. Eur. J. 2001, 7, 4854-4862.
32. (g) Adams, H.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Spey, S. E.; Urch, C. J.; Sanderson, J. M. Chem. Eur. J. 2001, 7, 4863-4877.
33. (h) Sindkhedkar, M. D.; Mulla, H. R.; Cammers-Goodwin, A. J. Am. Chem. Soc. 2000, 122, 9271-9277.
34. (i) Liu, D. H.; Williamson, D. A.; Kennedy, M. L.; Williams, T. D.; Morton, M. M.; Benson, D. R. J. Am. Chem. Soc. 1999, 121, 11798-11812.
35. (j) Heaton, N. J.; Bello, P.; Herradon, B.; del Campo, A.; Jimenez-Barbero, J. J. Am. Chem. Soc. 1998, 120, 12371-12384.
36. (k) Kim, E.; Paliwal, S.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 120, 11192-1193.
37. (a) Sinnokrot, M. O.; Sherrill, C. D. J. Phys. Chem. A 2004,108, 10200-10207.
38. (b) Sinnokrot, M. O.; Sherrill, C. D. J. Am. Chem. Soc. 2004, 126, 7690-7697.
39. (c) Morozov, A. V.; Misura, K. M. S.; Tsemekhman, K.; Baker, D. J. Phys. Chem. B 2004, 108, 8489-8496.
40. (d) Gervasio, F. L.; Chelli, R.; Procacci, P.; Schettino V. Proteins 2002, 48, 117-125.
41. (e) Tsuzuki, S.; Honda, K; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104-112 and references therein.
42. Struthers; M. D.; Cheng, R. P.; Imperiali, B. J. Am. Chem. Soc. 1996, 118, 3073-3081.
43. Mortishiresmith, R. J.; Lee M. S.; Bolinger, L.; Wright P. E. FEBS Lett. 1992, 296, 11-15.
44. Lachenmann, M. J.; Ladbury, J. E.; Phillips, N. B.; Narayana, N.; Qian, X. Q.; Stern, A. S.; Weiss, M. A. J. Mol. Biol. 2002, 376, 969-989.
45. Turk, J. A.; Smithrud, D. B. J. Org. Chem. 2001, 66, 8328-8335.
46. (a) Luppi, G.; Lanci, D.; Trigari, V.; Garavelli, M.; Garelli, A.; Tomasini, C. J. Org. Chem. 2003, 68, 1982-1993.
47. (b) Trabocchi, A.; Occhiato, E. G.; Potenza, D.; Guarna, A. J. Org. Chem. 2002, 68,1982-1993.
48. (c) Yang, J. H.; Christianson, L. A.; Gellman, S. H. Org. Lett. 1999, 1, 11-14.
49. (d) Nowick, J. S.; Mahrus, S.; Smith, E. M.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 1066-1072.
50. (e) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280-3281.
51. (f) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
52. (a) de la Paz, M. L.; Ellis, G.; Perez, M.; Perkins, J.; Jimenez-Barbero, J.; Vicent, C. Eur. J. Org. Chem. 2002, 840-855.
53. (b) Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2001, 123, 6819-6825.
54. (c) Belvisi, L.; Gennari, C.; Madder, A.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 695-699.
55. (d) Soth, M. J.; Nowick, J. S. J. Org. Chem. 1999, 64, 276-281.
56. (e) Smith, A. B.; Favor, D. A.; Sprengeler, P. A.; Guzman, M. C.; Carroll, P. J.; Furst, G. T.; Hirschmann, R. Bioorg. Med. Chem. 1999, 7, 9-22.
57. (f) Yang, J.; Gellman, S. H. J. Am. Chem. Soc. 1890, 12, 9090-9091.
58. (g) Jones, I. G.; Jones, W.; North, M. J. Org. Chem. 1998, 63, 1505-1513.
59. (h) Fowler, P.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1996, 79, 269-287.
60. (i) Vasella, A.; Witzig, C. Helv. Chim. Acta 1995, 78, 1971-1982.
61. Wavefunction, Inc.: Irvine, CA.
62. Burley, S. K; Petsko, G. A. Adv. Protein Chem. 1988, 39, 125-189.
63. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.