Sequence-specific recognition and cooperative dimerization of N-terminal aromatic peptides in aqueous solution by a synthetic host

Journal of the American Chemical Society

Volumn 128, Issue 38, 2006, Pages 12574-12581

  Heitmann, Lisa M ^a   Taylor, Alexander B ^b,c   Hart, P John ^b,c   Urbach, Adam R ^a  

^a TRINITY UNIVERSITY   (United States)

^b Mays Cancer Center at UT Health San Antonio   (United States)

^c UNIVERSITY OF TEXAS HEALTH SCIENCE CENTER AT SAN ANTONIO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CRYSTAL STRUCTURE; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEINS; SOLUTIONS;

AROMATIC PEPTIDES; BIOCHEMICAL PROCESSES; PEPTIDE SEQUENCE;

POLYPEPTIDES;

AROMATIC COMPOUND; PEPTIDE DERIVATIVE; TRYPTOPHAN;

AMINO TERMINAL SEQUENCE; AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL REACTION; CRYSTAL STRUCTURE; DIMERIZATION; ISOTHERMAL TITRATION CALORIMETRY; MOLECULAR RECOGNITION; PEPTIDE ANALYSIS; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS, AROMATIC; BRIDGED COMPOUNDS; CALORIMETRY; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; IMIDAZOLES; KINETICS; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; PROTEIN BINDING; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS; WATER;

EID: 33749180159     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064323s     Document Type: Article

References (61)

1. Peczuh, M. W.; Hamilton, A. D. Chem. Rev. 2000, 100, 2479-2493.
2. Bush, M. E.; Bouley, N. D.; Urbach, A. R. J. Am. Chem. Soc. 2005, 127, 14511-14517.
3. (a) Shepherd, J.; Gale, T.; Jensen, K. B.; Kilburn, J. D. Chem.-Eur. J. 2006, 12, 713-720.
4. (b) Tashiro, S.; Tominaga, M.; Kawano, M.; Therrien. B.; Ozeki, T.; Fujita, M. J. Am. Chem. Soc. 2005, 127, 4546-4547.
5. (c) Schmuck, C.; Heil, M.; Scheiber, J.; Baumann, K. Angew. Chem., Int. Ed. 2005, 44, 7208-7212.
6. (d) Buschmann, H.-J.; Mutihac, L.; Mutihac, R.-C.; Schollmeyer, E. Thermochim. Acta 2005, 430, 79-82.
7. (e) Wright, A. T.; Anslyn, E. V. Org. Lett. 2004, 6, 1341-1344.
8. (f) Ojida, A.; Mito-oka, Y.; Inoue, M.; Hamachi, I. J. Am. Chem. Soc. 2002, 124, 6256-6258.
9. (g) Sirish, M.; Schneider, H.-J. Chem. Commun. 1999, 907-908.
10. (h) Wagner, H.; Still, W. C.; Chen, C.-T. Science 1998, 279, 851-853.
11. (i) Hossain, M. A.; Schneider, H.-J. J. Am. Chem. Soc. 1998, 120, 11208-11209.
12. (j) Breslow, R.; Yang, Z.; Ching, R.; Trojandt, G.; Odobel, F. J. Am. Chem. Soc. 1998, 120, 3536-3537.
13. (a) Zhou, H.; Baldini, L.; Hong, J.; Wilson, A. J.; Hamilton, A. D. J. Am. Chem. Soc. 2006, 128, 2421-2425.
14. (b) Wright, A. T.; Anslyn, E. V.; McDevitt, J. T. J. Am. Chem. Soc. 2005, 127, 17405-17411.
15. (c) Buryak, A.; Severin, K. J. Am. Chem. Soc. 2005, 127, 3700-3701.
16. (a) Kiessling, L. L.; Gestwicki, J. E.; Strong, L. E. Angew. Chem., Int. Ed. 2006, 45, 2348-2368.
17. (b) Buskirk, A. R.; Liu, D. R. Chem. Biol. 2005, 12, 151-161.
18. (c) Kley, N. Chem. Biol. 2004, 11, 599-608.
19. (d) Berg, T. Angew. Chem., Int. Ed. 2003, 42, 2462-2481.
20. (e) Weiss, A.; Schlessinger, J. Cell 1998, 94, 277-280.
21. (f) Ho, S. N.; Biggar, S. R.; Spencer, D. M.; Schreiber, S. L.; Crabtree, G. R. Nature 1996, 382, 822-826.
22. (g) Spencer, D. M.; Wandless, T. J.; Schreiber, S. L.; Crabtree, G. R. Science 1993, 262, 1019-1024.
23. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
24. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.; Kim, K. Acc. Chem. Res. 2003, 36, 621-630.
25. (a) Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967.
26. (b) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. J. Am. Chem. Soc. 2005, 127, 12984-12989.
27. (c) Buschmann, H.-J.; Cleve, E.; Schollmeyer, E. Inorg. Chim. Acta 1992, 193, 93-97.
28. (d) Mock, W. L.; Shih, N.-Y. J. Am. Chem. Soc. 1988, 110, 4706-4710.
29. (e) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440-4446.
30. (f) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1983, 48, 3618-3619.
31. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540-541.
32. Day, A. I.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094-8100.
33. Liu, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798-16799.
34. (a) Jon, S. Y.; Selvapalam, N.; Oh, D. H.; Kang, J.-K.; Kim, S.-Y.; Jeon, Y. J.; Lee, J. W.; Kim, K. J. Am. Chem. Soc. 2003, 125, 10186-10187.
35. (b) Lee, H.-K.; Park, K. M.; Jeon, Y. J.; Kim, D.; Oh, D. H.; Kim, H. S.; Park, C. K.; Kim, K. J. Am. Chem. Soc. 2005, 127, 5006-5007.
36. (a) Isobe, H.; Sato, S.; Nakamura, E. Org. Lett. 2002, 4, 1287-1289.
37. (b) Day, A.; Arnold, A. P.; Blanch, R. J. Molecules 2003, 8, 74-84.
38. (c) Zhao, Y.; Xue, S.; Zhu, Q.; Tao, Z.; Zhang, J.; Wei, Z.; Long, L.; Hu, M.; Xiao, H.; Day, A. Chin. Sci. Bull. 2004, 49, 1111-1116.
39. (a) Isaacs, L.; Park, S.-K.; Liu, S.; Ko, Y. H.; Selvapalam, N.; Kim, Y.; Kim, H.; Zavalij, P. Y.; Kim, G.-H.; Lee, H.-S.; Kim, K. J. Am. Chem. Soc. 2005, 127, 18000-18001.
40. (b) Lagona, J.; Fettinger, J. C.; Isaacs, L. J. Org. Chem. 2005, 70, 10381-10392.
41. (c) Lagona, J.; Wagner, B. D.; Isaacs, L. J. Org. Chem. 2006, 71, 1181-1190.
42. (a) Blanch, R. J.; Sleeman, A. J.; White, J. T.; Arnold, A. P.; Day, A. I. Nano Lett. 2002, 2, 147-149.
43. (b) Kim, H.-J.; Jeon, W. S.; Ko, Y. H.; Kim, K. PNAS 2002, 99, 5007-5011.
44. (c) Ong, W.; Gomez-Kaifer, M.; Kaifer, A. E. Org. Lett. 2002, 4, 1791-1794.
45. (d) Sindelar, V.; Moon, K.; Kaifer, A. E. Org. Lett. 2004, 6, 2665-2668.
46. (a) Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526-1529.
47. (b) Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938-1939.
48. (c) Jeon, W. S.; Kim, H.; Lee, C.; Kim, K. Chem. Commun. 2002, 1828-1829.
49. (d) Ziganshina, A.; Ko, Y. H.; Jeon, W. S.; Kim, K. Chem. Commun. 2004, 806-807.
50. (e) Sindelar, V.; Cejas, M. A.; Raymo, F. M.; Chen, W.; Parker, S.; Kaifer, A. E. Chem.-Eur. J. 2005, 11, 7054-7059.
51. We focused on the aromatic amino acids for the likelihood that their binding properties would be similar in nature to prior work in this area and, therefore, more straightforward to characterize.
52. We studied Gly-Gly-Gly as a control for the possible binding of Gly residues to Q8 and, as expected, found no binding to Q8 by ITC (see Supporting Information).
53. 2 are described as "positively cooperative" due to their shape. The binding experiments show that saturation occurs at a 2:1 peptide:Q8 ratio. The isotherms show a single prominent sigmoidal phase at approximately this ratio. This characteristic indicates that the second stepwise equilibrium association constant is either greater than or equal to the first. In addition, all experiments show a characteristic, shallow "smile" early in the titration (at left), indicating that the first binding transition is less steep (and thus the first K value is smaller) than the second.
54. Tochtrop, G. P.; Richter, K.; Tang, C.; Toner, J. J.; Covey, D. F.; Cistola, D. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1847-1852.
55. Connors, K. A. Binding Constants. The Measure of Molecular Complex Stability; John Wiley & Sons, Inc.: New York, 1987.
56. Williams, D. H.; Stephens, E.; O'Brien, D.; Zhou, M. Angew. Chem., Int. Ed. 2004, 43, 6596-6616.
57. The distinguishing factor between this hydrogen bond and the other close (≤3.1 Å) dipole-dipole interactions described is the N-H-O angle of 163°, which is significantly above a cutoff of 140°.
58. Otwinowski, Z.; Minor, W. In International Tables for Crystallography, Rossman, M., Arnold, W., Eds.; Kluwer: Dordrecht, The Netherlands, 2001; Vol. F.
59. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 2005, 38, 381-388.
60. Emsley, P.; Cowtan, K. Acta Crystallogr. 2004, D60, 2126-2132.
61. Sheldrick, G. M.; Schenider, T. R. Methods Enzymol. 1997, 277, 319-343.