Design, synthesis and evaluation of synthetic receptors for the recognition of aspartate pairs in an α-helical confirmation

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 8, 1997, Pages 1455-1467

  Albert, Jeffrey S ^a   Peczuh, Mark W ^a   Hamilton, Andrew D ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARTIC ACID DERIVATIVE; PEPTIDE; RECEPTOR;

ALPHA HELIX; ARTICLE; BINDING AFFINITY; CIRCULAR DICHROISM; MOLECULAR RECOGNITION; PROTEIN CONFORMATION; RECEPTOR BINDING; SYNTHESIS;

AMINO ACID SEQUENCE; ASPARTIC ACID; CIRCULAR DICHROISM; DRUG DESIGN; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; RECEPTORS, CELL SURFACE;

EID: 0342327314     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00086-2     Document Type: Article

References (46)

1. Silverman, R. B. Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC: Boca Raton, FL, 1988.
2. See, for example: (a) Nassar, N.; Horn, G.; Herrmann, C.; Scherer, A.; McCormick, F.; Wittinghofer, A. Nature 1995, 375, 554.
3. (b) Lilley, D. M. J. DNA-Protein: Structural Interactions; Oxford University Press: Oxford, 1995.
4. (c) Pruschy, M. N.; Spencer, D. M.; Kapoor, T. M.; Miyake, H.; Crabtree, G. R.; Schreiber, S. L. Chem. & Biol. 1994, 1, 163.
5. Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.
6. Öspay, G.; Taylor, J. W. J. Am. Chem. Soc. 1992, 114, 6966.
7. Jackson, D. Y.; King, D. S.; Chmielewski, J.; Singh, S.; Schultz, P. G. J. Am. Chem. Soc. 1991, 113, 9391.
8. (a) Lyu, P. C.; Marky, L. A.; Kallenbach, N. R. J. Am. Chem. Soc. 1989, 111, 2733.
9. (b) Marqusee, S.; Baldwin, R. L. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8898.
10. (a) Ghadiri, M. R.; Fernholz, A. K. J. Am. Chem. Soc. 1990, 112, 9633.
11. (b) Ruan, F.; Chen, Y.; Hopkins, P. B. J. Am. Chem. Soc. 1990, 112, 9403.
12. (a) Albert, J. S.; Hamilton, A. D. Biochem. 1995, 34, 984.
13. (b) Shoemaker, K. R.; Fairman, R.; Schultz, D. A.; Robertson, A. D.; York, E. J.; Stewart, J. M.; Baldwin, R. L. Biopolymers 1990, 29, 1.
14. Voyer, N.; Deschênes, D.; Bernier, J.; Roby, J. J. Chem. Soc. Chem. Comm. 1992, 134.
15. Mallik, S.; Plunkett, S. D.; Dhal, P. K.; Johnson, R. D.; Pack, D.; Shnek, D.; Arnold, F. H. New J. Chem. 1994, 18, 299.
16. Tabet, M.; Labroo, V.; Sheppard, P.; Sasaki, T. J. Am. Chem. Soc. 1993, 115, 386.
17. Pavletich, N. P.; Pabo, C. O. Science 1991, 252, 809.
18. Luisi, B. F.; Xu, W. X.; Otwinowski, Z.; Freedman, L. P.; Yamamoto, K. R.; Sigler, P. B. Nature 1991, 352, 497.
19. (a) Constant, J. F.; Fahy, J.; Lhomme, J. Tetrahedron Lett. 1987, 28, 1777.
20. (b) Faruta, H.; Magda, D.; Sessler, J. L. J. Am. Chem. Soc. 1991, 113, 978.
21. (c) Kato, Y.; Conn, M. M.; Rebek, J. Jr. J. Am. Chem. Soc. 1994, 116, 3279.
22. (d) Kneeland, D. M.; Ariga, K.; Lynch, V. M.; Huang, C.-Y.; Anslyn, E. V. J. Am. Chem. Soc. 1993, 115, 10042.
23. (e) Williams, D. H.; Searle, M. S.; Mackay, J. P.; Gerhard, U.; Maplestone, R. A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1172.
24. (a) Bernardo, A. R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1992, 114, 10624.
25. (b) Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907.
26. (c) Lehn, J.-M. Angew. Chem. Int. Ed. Engl. 1988, 27, 87.
27. (d) Lehn, J.-M.; Méric, R.; Vigneron, J.-P.; Bkouche-Waksman, I.; Pascard, C. J. Chem. Soc. Chem. Comm. 1991, 62.
28. (e) Odashima, K.; Itai, A.; Iitaka, Y.; Koga, K. J. Am. Chem. Soc. 1980, 102, 2504.
29. (f) Schneider, H.-J.; Schiestel, T.; Zimmermann, P. J. Am. Chem. Soc. 1992, 114, 7698.
30. (g) Tabushi, I.; Yamamura, K.; Nonoguchi, H.; Hirotsu, K.; Higuchi, T. J. Am. Chem. Soc. 1984, 106, 2621.
31. (h) Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554.
32. (a) Schießl, P.; Schmidtchen, F. P. Tetrahedron Lett. 1993, 34, 2449.
33. (b) Schießl, P.; Schmidtchen, F. P. J. Org. Chem. 1994, 59, 509.
34. Albert, J. S.; Goodman, M. S.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 1143.
35. Huyghues-Despointes, B. M. P.; Scholtz, J. M.; Baldwin, R. L. Prot. Sci. 1993, 2, 1604.
36. Woody, R. W. In The Peptides: Analysis, Synthesis, Biology; Udenfriend, S.; Meienhofer, J., Eds.; Academic Press: Orlando, FL, 1985; Vol. 7, pp 15-114.
37. Bernatowicz, M. S.; Wu, Y.; Matsucda, G. R. Tetrahedron Lett. 1993, 34, 3389.
38. Rasmussen, C. R.; Villani, F. J.; Reynolds, B. E.; Plampin, J. N.; Hood, A. R.; Hecker, L. R.; Nortey, S. O.; Hanslin, A.; Costanzo, M. J.; House, R. M.; Molinari, A. J. Synthesis 1988, 460.
39. Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933.
40. Chakrabartty, A.; Baldwin, R. L. In Protein Folding: In Vivo and In Vitro; Cleland, J. L., Ed.; American Chemical Society: Washington, DC, 1993; pp 166-177.
41. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem . 1990, 11, 440.
42. Brandts, J. F.; Kaplan, L. J. Biochem. 1973, 12, 2011.
43. Chakrabartty, A.; Schellman, J. A.; Baldwin, R. L. Nature (London) 1991, 351, 586.
44. Wilcox, C. S. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H. J.; Dürr, H., Eds.; VCH, Weinheim, 1990; pp 123-143. We are grateful for Professor Wilcox's provision and support of the HOSTEST computational tools.
45. Bertz, S. H.; Cook, J. M.; Gawish, A.; Weiss, U. Org. Synth. 1986, 64, 27.
46. Camps, P.; Iglesias, C.; Lazano, R.; Miranda, M. A.; Rodríguez, M. J. Tetrahedron Lett. 1987, 28, 1831.