Stereoselective synthesis of individual isomers of Leu-enkephalin analogues containing substituted β-turn bicyclic dipeptide mimetics

Chemical Communications

Volumn 3, Issue 13, 2003, Pages 1598-1599

  Xiong, Chiyi ^a   Zhang, Junyi ^a   Davis, Peg ^b   Wang, Wei ^a,c   Ying, Jinfa ^a   Porreca, Frank ^b   Hruby, Victor J ^a  

^a University of Arizona   (United States)

^b UNIVERSITY OF ARIZONA   (United States)

^c GENOMICS INSTITUTE OF THE NOVARTIS RESEARCH FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 PHENYLTHIAINDOLIZIDINONE AMINO ACID; AMINO ACID; DIPEPTIDE; GLYCINE; LEUCINE ENKEPHALIN DERIVATIVE; PHENYLALANINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; ISOMERISM; PROTEIN INTERACTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0038480737     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b302235h     Document Type: Article

References (23)

1. L. Halab, F. Gosselin, W. D. Lubell, Biopolymers (Peptide Sci.), 2000, 55, 101
2. S. Hanessian, G. McNaughton-Smith, H.-G. Lombart, W. D. Lubell, Tetrahedron, 1997, 53, 12789
3. T. D. W. Claridge, H. Christopher, J. K. Richard, L. Victor, A. N. Ian, J. S. Christopher, Bioorg. Med. Chem. Lett., 1996, 6, 485
4. U. Nagai, S. Kazuki, N. Rika, K. Rika, Tetrahedron, 1993, 49, 3577
5. M. Eguchi, R. Y. W. Shen, J. P. Shea, M. S. Lee, M. Kahn, J. Med. Chem., 2002, 45, 1395
6. Y. Rew, M. Goodman, J. Org. Chem., 2002, 67, 8820
7. B. Vesterman, J. Saulitis, J. Betins, E. Liepins, G. V. Nikiforovich, Biochim. Biophys. Acta, 1989, 998, 204
8. V. J. Hruby, C. A. Gehrig, Med. Res. Rev., 1989, 9, 343
9. R. Schwyzer, P. Moutevelis-Minakakis, S. Kimura, H.-U. Gremlich, J. Peptide Sci., 1997, 3, 65
10. E. R. Stimson, Y. C. Meinwald, H. A. Scheraga, Biochemistry, 1979, 18, 1661
11. H. I. Mosberg, R. Hurst, V. J. Hruby, K. Gee, H. I. Yamamura, J. J. Galligan, T. F. Burks, Proc. Natl. Acad. Sci. USA, 1983, 80, 5871
12. V. J. Hruby, L.-F. Kao, B. M. Pettitt, M. Karplus, J. Am. Chem. Soc., 1988, 110, 3351
13. A. Bach II, J. A. Markwalder, W. C. Ripka, Int. J. Peptide Protein Res., 1991, 38, 314
14. S. Roy, H.-G. Lombart, W. D. Lubell, R. E. W. Hancock, S. W. Farmer, J. Peptide Res., 2002, 60, 198
15. W. Li, K. D. Moeller, J. Am. Chem. Soc., 1996, 118, 10106
16. S. Hanessian, G. McNaughton-Smith, Bioorg. Med. Chem. Lett., 1996, 6, 1567
17. S. Y. Tamura, E. A. Goldman, T. K. Brunck, W. C. Ripka, J. E. Semple, Bioorg. Med. Chem. Lett., 1997, 7, 331
18. F. Gosselin, D. Tourwe, M. Ceusters, T. Meert, L. Heylen, M. Jurzak, W. D. Lubell, J. Peptide Res., 2001, 57, 337
19. C. Xiong, W. Wang, C. Cai, V. J. Hruby, J. Org. Chem., 2002, 67, 1399
20. C. Xiong, W. Wang, V. J. Hruby, J. Org. Chem., 2002, 67, 3514
21. A. M. Felix, J. Org. Chem., 1974, 39, 1427
22. P. G. Mattingly, M. J. Miller, J. Org. Chem., 1981, 46, 1557
23. M. Wakselman, M. Zrihen, Chem. Lett., 1982, 3, 333