Synthesis of a novel β-turn mimetic and its incorporation in Leu- enkephalin

Tetrahedron Letters

Volumn 40, Issue 33, 1999, Pages 6113-6116

  Kreye, Paul ^a   Kihlberg, Jan ^a  

^a UMEÅ UNIVERSITY   (Sweden)

Author keywords

Amino acids; Medium ring heterocycles; Peptide mimetics

Indexed keywords

GONADORELIN; LEUCINE ENKEPHALIN; PEPTIDE; SOMATOSTATIN;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CONFORMATIONAL TRANSITION; HYDROGEN BOND; OXIDATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033551755     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01216-2     Document Type: Article

References (20)

1. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Turns in peptides and proteins. In Advances in Protein Chemistry; Anfinsen, C. B.; Edsall, J. T.; Richards, F. M. Eds.; Academic Press: Orlando, Florida, 1985; Vol. 37; pp. 1-109.
2. Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55-64.
3. Hölzemann, G. Kontakte (Darmstadt) 1991, 3-12, 55-63.
4. Kahn, M. Synlett 1993, 821-826.
5. Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
6. Liskamp, R. M. J. Recl. Trav. Chim. Pays-bas 1994, 113, 1-19.
7. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789- 12854.
8. Smith, G. D.; Griffin, J. F. Science 1978, 199, 1214-1216.
9. Amodeo, P.; Naider, F.; Picone, D.; Tancredi, T.; Temussi, P. A. J. Peptide Sci. 1998, 4, 253-265.
10. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
11. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
12. Hanessian, S.; Park, H.; Yang, R.-Y. Synlett 1997, 353-354.
13. Alper, P. B.; Hung, S.-C; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
14. 3).
15. Pietraszkiewicz, M.; Jurczak, J. Tetrahedron 1984, 40, 2967-2970.
16. Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1987, 28, 6331-6334.
17. Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. Heterocycles 1988, 27, 1241-1248.
18. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849-3862.
19. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201- 203.
20. Jakubke, H.-D. Peptide: Chemie Und Biologie; Spektrum Akad. Verl.: Heidelberg, 1996; pp. 256-258.