A Reverse Turn Structure Induced by a D,L-α-Aminoxy Acid Dimer

Journal of the American Chemical Society

Volumn 125, Issue 47, 2003, Pages 14452-14457

  Yang, Dan ^a   Qu, Jin ^a   Li, Wei ^a   Wang, De Ping ^b   Ren, Yi ^b   Wu, Yun Dong ^b  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DIMERS; HYDROGEN BONDS; QUANTUM THEORY; SUBSTITUTION REACTIONS; X RAY ANALYSIS;

HETEROCHIRAL COMPOUNDS;

AMINO ACIDS;

ALANINE; AMIDE; AMINO ACID DERIVATIVE; DIMER; DIMETHYL SULFOXIDE; GLYCINE; PEPTIDE;

AMINO ACID ANALYSIS; AMINO TERMINAL SEQUENCE; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; CHIRALITY; DATA ANALYSIS; DILUTION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; SEQUENCE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY ANALYSIS;

AMINO ACIDS; DIMERIZATION; HYDROGEN BONDING; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY;

EID: 0345306283     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029514j     Document Type: Article

References (70)

1. (a) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
2. (b) Chou, P. Y.; Fasman, G. D. J. Mol. Biol. 1977, 115, 135.
3. (c) Sibanda, B. L.; Thornton, J. M. Nature 1985, 316, 170.
4. (d) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221.
5. (e) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1.
6. For recent reviews on reverse turn mimics, see: (a) Ball, J. B.; Alewood, P. F. J. Mol. Recognit. 1990, 3, 55.
7. (b) Kahn, M. Synlett 1993, 11, 821.
8. (c) Müller, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2767.
9. (d) Gillespie, P.; Cicariello, J.; Olson, G. L. Biopolymers 1997, 43, 191.
10. (e) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
11. (f) Stigers, K. D.; Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1999, 3, 714.
12. (g) Burgess, K. Acc. Chem. Res. 2001, 34, 826.
13. For recent examples of ring-fused or macrocyclic reverse turn mimics, see: (a) Eguchi, M.; Shen, R. Y. W.; Shea, J. P.; Lee, M. S.; Kahn, M. J. Med. Chem. 2002, 45, 1395.
14. (b) Jiang, L.; Burgess, K. J. Am. Chem. Soc. 2002, 124, 9028.
15. (c) Banerji, B.; Bhattacharya, M.; Madhu, R. B.; Das, S. K.; Iqbal, J. Tetrahedron Lett. 2002, 43, 6473.
16. (d) Wels, B.; Kruijtzer, J. A. W.; Liskamp, R. M. J. Org. Lett. 2002, 4, 2173.
17. (e) Sukopp, M.; Marinelli, L.; Brandl, T.; Goodman, S. L.; Hoffmann, R. W.; Kessler, H. Helv. Chim. Acta 2002, 85, 4442.
18. (f) Cheng, R. P.; Suich, D. J.; Cheng, H.; Roder, H.; DeGrado, W. F. J. Am. Chem. Soc. 2001, 123, 12710.
19. (g) Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 256.
20. (h) De Borggraeve, W. M.; Rombouts, F. J. R.; Van der Eycken, E. V.; Toppet, S. M.; Hoornaert, G. J. Tetrahedron Lett. 2001, 42, 5693.
21. (i) Gademann, K.; Ernst, M.; Seebach, D.; Hoyer, D. Helv. Chim. Acta 2000, 83, 16.
22. (j) Estiarte, M. A.; Rubiralta, M.; Diez, A.; Thormann, M.; Giralt, E. J. Org. Chem. 2000, 65, 6992.
23. (k) MacDonald, M.; Vander Velde, D.; Aube, J. Org. Lett. 2000, 2, 1653.
24. (l) Feng, Y.-B.; Pattarawarapan, M.; Wang, Z.-C.; Burgess, K. J. Org. Chem. 1999, 64, 9175.
25. (m) Eguchi, M.; Lee, M. S.; Nakanishi, H.; Stasiak, M.; Lovell, S.; Kahn, M. J. Am. Chem. Soc. 1999, 121, 12204.
26. (n) Haskell-Luevano, C.; Rosenquist, A.; Souers, A.; Khong, K. C.; Ellman, J. A.; Cone, R. D. J. Med. Chem. 1999, 42, 4380.
27. (o) Souers, A. J.; Virgilio, A. A.; Rosenquist, Å.; Fenuik, W.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 1817.
28. (p) Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334.
29. (q) Ranganathan, D.; Haridas, V.; Kurur, S.; Thomas, A.; Madhusudanan, K. P.; Nagaraj, R.; Kunwar, A. C.; Sarma, A. V. S.; Karle, I. L. J. Am. Chem. Soc. 1998, 120, 8448.
30. (r) Feng, Y.-B.; Wang, Z.-C.; Jin, S.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 10768.
31. (s) Souers, A. J.; Virgilio, A. A.; Schurer, S.; Ellman. J. A.; Kogan, T. P.; West, H. E.; Ankener, W.; Vanderslice, P. Bioorg. Med. Chem. Lett. 1998, 8, 2297.
32. (t) Bach, A. C., II; Espina, J. R.; Jackson, S. A.; Stouten, P. F. W.; Duke, J. L.; Mousa, S. A.; DeGrado, W. F. J. Am. Chem. Soc. 1996. 118, 293.
33. (u) Haubner, R.; Schmitt, W.; Holzemann, G.; Goodman, S. L.; Jonczyk, A. ; Kessler, H. J. Am. Chem. Soc. 1996, 118, 7881.
34. (v) Virgilio, A. A.; Bray, A. A.; Zhang, W.; Trinh, L.; Snyder, M.; Morrissey, M. M.; Ellman, J. A. Tetrahedron 1996, 53, 6635.
35. (w) Kim, K.; Dumas, J.-P.; Germanas, J. P. J. Org. Chem. 1996, 61, 3138.
36. (x) Hoffmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62.
37. (y) Rombouts, F. J. R.; De Borggraeve, W. M.; Delaere, D.; Froeyen, M.; Toppet, S. M.; Compernolle, F,; Hoornaert, G. J. Eur. J. Org. Chem. 2003, 1868.
38. For reverse turn mimics based on β-amino acids, see: (a) Seebach, D.; Abele, S.; Gademann, K.; Jaun, B. Angew. Chem., Int. Ed. 1999, 38, 1595.
39. (b) Seebach, D.; Abele, S.; Sifferlen, T.; Hänggi, M.; Gruner, S.; Seiler, P. Helv. Chim. Acta 1998, 81, 2218.
40. (c) Chung, Y.-J.; Christianson, L. A.; Stanger, H. E.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 10555.
41. (d) Huck, B. R.; Fisk, J. D.; Gellman, S. H. Org. Lett. 2000, 2, 2607.
42. (e) Chung, Y.-J.; Huck, B. R.; Christianson, L. A.; Stanger, H. E.; Krauthäuser, S.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 3995.
43. (f) Arnold, U.; Hinderaker, M. P.; Nilsson, B. L.; Huck, B. R.; Gellman, S. H.; Raines, R. T. J. Am. Chem. Soc. 2002, 124, 8522-8523.
44. (g) Langenhan, J. M.; Guzei, I. A.; Gellman, S. H. Angew. Chem., Int. Ed. 2003, 42, 2402.
45. For reverse turn mimics based on γ-amino acids or δ-amino acids, see: (a) Hanessian, S.; Luo, X.-H.; Schaum, R. Tetrahedron Lett. 1999, 40, 4925.
46. (b) Woll, M. G.; Lai, J. R.; Guzei, I. A.; Taylor, S. J. C.; Smith, M. E. B.; Gellman, S. H. J. Am. Chem. Soc. 2001, 123, 11077.
47. (c) Brenner, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 2155.
48. (d) Cheung, E. Y.; McCabe, E. E.; Harris, K. D. M.; Johnston, R. L.; Tedesco, E.; Raja, K. M. P.; Balaram, P. Angew. Chem., Int. Ed. 2002, 41, 494.
49. (e) Nowick, J. S.; Brower, J. O. J. Am. Chem. Soc. 2003, 125, 876.
50. For reverse turn mimics based on pyrrolinones, see: Smith, A. B., III; Wang, W.; Sprengeler, P. A.; Hirschmann, R. J. Am. Chem. Soc. 2000, 122, 11037.
51. For recent reviews on the secondary structures of unnatural oligomers, see: (a) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
52. (b) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
53. (c) Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1997, 1, 120.
54. (d) Stigers, K. D.; Soth, M. J.; Nowick, J. S. Curr. Opin. Chem. Biol. 1999, 3, 714.
55. (e) Kirshenbaum, K.; Zuckermann, R. N.; Dill, K. A. Curr. Opin. Struct. Biol. 1999, 9, 530.
56. (f) Gademann, K.; Hintermann, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905.
57. (g) DeGrado, W. F.; Hamuro, Y. J. Pept. Res. 1999, 54, 206.
58. (h) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
59. (a) Yang, D.; Ng, F.-F.; Li, Z.-J.; Wu, Y.-D.; Chan, K. W.-K.; Wang, D.-P. J. Am. Chem. Soc. 1996, 118, 9794.
60. (b) Yang, D.; Li, B.; Ng, F.-F.; Yan, Y.-L.; Qu, J.; Wu, Y.-D. J. Org. Chem. 2001, 66, 7303.
61. (a) Yang, D.; Qu, J.; Li, B.; Ng, F.-F.; Wang, X.-C.; Cheung, K.-K.; Wang, D.-P.; Wu, Y.-D. J. Am. Chem. Soc. 1999, 121, 589.
62. (b) Wu, Y.-D.; Wang, D.-P.; Chan, K. W. K.; Yang, D. J. Am. Chem. Soc. 1999, 121, 11189.
63. (c) Peter, C.; Daura, X.; Van Gunsteren, W. F. J. Am. Chem. Soc. 2000, 122, 7461.
64. See Supporting Information for details.
65. Liang, G. B.; Rito, C. J.; Gellman, S. H. J. Am. Chem. Soc. 1992, 114, 4440.
66. (a) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2847.
67. (b) Kim, K.; Germanas, J. P. J. Org. Chem. 1997, 62, 2853.
68. The chemical shift changes for amide protons of 4 in the concentration range of 0.1-1 mM were below 0.02 ppm, indicating that no aggregation of 4 occurred at 1 mM (see Supporting Information).
69. All calculations were performed with: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; AI-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W. Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A7M; Gaussian, Inc.: Pittsburgh, PA, 1998. Cartesian coordinates of structures 1, 2, 2′, and 7 are given in the Supporting Information. The relative energies of 2 and 2′ were calculated with the B3LYP/6-31G** method.
70. Yang, D.; Qu, J.; Li, W.; Zhang, Y.-H.; Wang, D.-P.; Wu, Y.-D. J. Am. Chem. Soc. 2002, 124, 12410.