Solid phase synthesis of C-terminal carbohydrate modified enkephalins

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 17, 1997, Pages 2247-2250

  Drouillat, Bruno ^a   Kellam, Barrie ^a   Dekany, Gyula ^a   Starr, Mike S ^a   Toth, Istvan ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; DELTA OPIATE RECEPTOR; ENKEPHALIN DERIVATIVE; LEUCINE ENKEPHALINAMIDE; METENKEPHALIN; NALTRINDOLE;

ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; REACTION ANALYSIS; SYNTHESIS;

EID: 0030928649     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00395-8     Document Type: Article

References (29)

1. For reviews see: a) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555.
2. b) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron 1996, 52, 4527.
3. b) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2289. Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron 1996, 52, 4527.
4. a) Frechet, J.M.; Schuerch, J. J. Am. Chem. Soc. 1971, 93, 492.
5. b) Guthrie, R.D.; Jenkins, A.D.; Roberts, G.A.F. J. Chem. Soc., Perkin Trans. I. 1973, 1, 2441.
6. c) Randolph, J.T.; McClure, K.F.; Danishefsky, S.J. J. Am. Chem. Soc. 1995, 117, 5712.
7. d) Roberge, J.Y.; Beebe, X.; Danishefsky, S.J. Science, 1995, 269, 202.
8. e) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc. 1995, 117, 2116.
9. f) Yan, L.; Taylor, C.M.; Goodnow Jr. R.; Kahne, J. J. Am. Chem. Soc. 1994, 116, 6953.
10. g) Radmann, J.; Schmidt, R.R. Tetrahedron Lett. 1996, 37, 3989.
11. h) Adinolfi, M.; Barone, G.; De Napoli, L.; Iadonisi, A.; Piccialli, G. Tetrahedron Lett. 1996, 37, 5007.
12. Hughes, J.; Smith, T.W.; Kosterlitz, H.W.; Fothergill, L.A.; Morgon, B.A.; Morris, R. Nature 1975, 258, 577.
13. a) Martin, W.R.; Eades, C.G.; Thompson, J.A.; Huppler, R.A.; Gilbert, P.E. J. Pharmacol. Exp. Ther. 1976, 197, 517.
14. b) Lord, J.A.H.; Waterfield, A.A.; Hughes, J.; Kosterlitz, H.W. Nature 267, 267, 495.
15. Hruby, V.J.; Gehrig, C.A. Med. Res. Rev. 1989, 9, 343.
16. a) Varga-Defterdarovic, L.; Horvat, S.; Chung, N.N.; Schiller, P.W. Int. J. Peptide Protein Res. 1992, 39, 12.
17. b) Horvat, S.; Horvat, J.; Varga-Defterdarovic, L.; Pavelic, K.; Chung, N.N.; Schiller, P.W. Int. J. Peptide Protein Res. 1993, 41, 399.
18. Bell, G.I.; Burant, C.F.; Takeda, J.; Gould, G.W. J. Biol. Chem. 1993, 268, 19161.
19. Mulder, G.J. Trends Pharmacol. Sci. 1992, 13, 302.
20. Kartha, K.P.R.; Aloui, M.; Field, R.A. XVIII Int. Carbohydrate Symp. Milan 1996, Abstract BP 271.
21. Gyorgdydeak, Z.; Szilagyi, L.; Paulsen, H. J. Carbohydrate Chem. 1993, 12, 139.
22. + (100).
23. Bayley, H.; Standring, D.N.; Knowles, J.R. Tetrahedron Lett. 1978, 19, 3633.
24. Knorr, R.; Trzeciak, W.; Bannworth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
25. + (15).
26. Hancock, W.S.; Battersby, J.E. Anal. Biochem. 1976, 71, 260.
27. + (64)
28. Rink, K. Tetrahedron Lett. 1987, 28, 3787.
29. + (46).