β2,3-cyclic aminoxy acids: Rigid and ring-size-independent building blocks of foldamers

Angewandte Chemie - International Edition

Volumn 43, Issue 48, 2004, Pages 6719-6722

  Yang, Dan ^a   Zhang, Dan Wei ^b   Hao, Yu ^a   Wu, Yun Dong ^c   Luo, Shi Wei ^c   Zhu, Nian Yong ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

^b FUDAN UNIVERSITY   (China)

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

Author keywords

Foldamers; Helical structures; Peptides; Secondary structure; Structure elucidation

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; COMPLEXATION; MOLECULAR STRUCTURE;

AMINOXY ACIDS; FOLDAMERS; PEPTIDES;

POLYPEPTIDES;

AMINOXY ACID; BETA AMINO ACID; PEPTIDE; UNCLASSIFIED DRUG;

ALPHA HELIX; ARTICLE; CHIRALITY; DILUTION; HYDROGEN BOND; PROTEIN FOLDING; PROTEIN SECONDARY STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TITRIMETRY;

EID: 10944263106     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454140     Document Type: Article

References (38)

1. a) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173;
2. b) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893.
3. a) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219;
4. b) P. I. Arvidsson, M. Rueping, D. Seebach, Chem. Commun. 2001, 7, 649;
5. c) D. Seebach, S. Abele, K. Gademann, B. Jaun, Angew. Chem. 1999, 111, 1700; Angew. Chem. Int. Ed. 1999, 38, 1595;
6. c) D. Seebach, S. Abele, K. Gademann, B. Jaun, Angew. Chem. 1999, 111, 1700; Angew. Chem. Int. Ed. 1999, 38, 1595;
7. d) K. Gademann, A. Häne, M. Rueping, B. Jaun, D. Seebach, Angew. Chem. 2003, 115, 1573; Angew. Chem. Int. Ed. 2003, 42, 1534;
8. d) K. Gademann, A. Häne, M. Rueping, B. Jaun, D. Seebach, Angew. Chem. 2003, 115, 1573; Angew. Chem. Int. Ed. 2003, 42, 1534;
9. e) J. M. Langenhan, I. A. Guzei, S. H. Gellman, Angew. Chem. 2003, 115, 2504; Angew. Chem. Int. Ed. 2003, 42, 2402.
10. e) J. M. Langenhan, I. A. Guzei, S. H. Gellman, Angew. Chem. 2003, 115, 2504; Angew. Chem. Int. Ed. 2003, 42, 2402.
11. a) D. H. Appella, L. A. Christianson, I. L. Karle, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1996, 118, 13071;
12. b) D. H. Appella, L. A. Christianson, D. A. Klein, D. R. Powell, X. Huang, J. J. Barchi, Jr., S. H. Gellman, Nature 1997, 387, 381;
13. c) D. H. Appella, L. A. Christianson, D. A. Klein, M. R. Richards, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1999, 121, 7574;
14. d) D. H. Appella, L. A. Christianson, I. L. Karle, D. R. Powell, S. H. Gellman, J. Am. Chem. Soc. 1999, 121, 6206;
15. e) J. J. Barchi, Jr., X. Huang, D. H. Appella, L. A. Christianson, S. R. Durell, S. H. Gellman, J. Am. Chem. Soc. 2000, 122, 2711.
16. a) D. H. Appella, J. J. Barchi, Jr., S. R. Durell, S. H. Gellman, J. Am. Chem. Soc. 1999, 121, 2309;
17. b) X. Wang, J. F. Espinosa, S. H. Gellman, J. Am. Chem. Soc. 2000, 122, 4821;
18. c) T. L. Raguse, J. R. Lai, P. R. LePlae, S. H. Gellman, Org. Lett. 2001, 3, 3963;
19. d) H.-S. Lee, F. A. Syud, X. Wang, S. H. Gellman, J. Am. Chem. Soc. 2001, 123, 7721;
20. e) M. G. Woll, J. D. Fisk, P. R. LePlae, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 12447;
21. f) E. A. Porter, X. Wang, M. A. Schmitt, S. H. Gellman, Org. Lett. 2002, 4, 3317.
22. a) P. R. LePlae, J. D. Fisk, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 6820;
23. b) T. L. Raguse, E. A. Porter, B. Weisblum, S. H. Gellman, J. Am. Chem. Soc. 2002, 124, 12447;
24. c) T. L. Raguse, J. R. Lai, S. H. Gellman, J. Am. Chem. Soc. 2003, 125, 5592;
25. d) J.-S. Park, H.-S. Lee, J. R. Lai, B. M. Kim, S. H. Gellman, J. Am. Chem. Soc. 2003, 125, 8539.
26. Y. D. Wu, D. P. Wang, J. Am. Chem. Soc. 1998, 120, 13485.
27. a) D. Yang, F. F. Ng, Z. J. Li, J. Am. Chem. Soc. 1996, 118, 9794;
28. b) D. Yang, J. Qu, B. Li, F. F. Ng, X. C. Wang, K. K. Cheung, D. P. Wang, Y. D. Wu, J. Am. Chem. Soc. 1999, 121, 589;
29. c) Y. D. Wu, D. P. Wang, K. W. K. Chan, D. Yang, J. Am. Chem. Soc. 1999, 121, 11 189;
30. d) D. Yang, J. Qu, W. Li, Y. H. Zhang, Y. Ren, D. P. Wang, Y. D. Wu, J. Am. Chem. Soc. 2002, 124, 12410.
31. CCDC-250085 and CCDC-250086 (3 and 4) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
32. a) D. Yang, Y. H. Zhang, N. Y. Zhu, J. Am. Chem. Soc. 2002, 124, 9966;
33. b) D. Yang, Y.-H. Zhang, B. Li, D.-W. Zhang, J. C.-Y. Chan, S.-W. Luo, Y.-D. Wu, N.-Y. Zhu, J. Am. Chem. Soc. 2004, 126, 6956.
34. For details of the calculation method and results, see the Supporting Information.
35. D. P. Dado, S. H. Gellman, J. Am. Chem. Soc. 1994, 116, 1054.
36. D. Seebach, M. Brenner, M. Rueping, B. Jaun, Chem. Eur. J. 2002, 8, 573.
37. a) S. Hanessian, X. Luo, R. Schaum, S. Michnick, J. Am. Chem. Soc. 1998, 120, 8569;
38. b) T. Hintermann, K. Gademann, B. Jaun, D. Seebach, Helv. Chim. Acta 1998, 81, 983.