Development of a model for the δ-opioid receptor pharmacophore. 4. Residue 3 dehydrophenylalanine analogues of Tyr-C[D-Cys-PheD-Pen]OH (JOM-13) confirm required gauche orientation of aromatic side chain

Biopolymers

Volumn 39, Issue 3, 1996, Pages 287-296

  Mosberg, Henry I ^a   Dua, Rajesh K ^a   Pogozheva, Irina D ^a   Lomize, Andrei L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CHEMICAL BONDS; CONFORMATIONS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

AROMATIC SIDE CHAINS; BINDING AFFINITY; DEHYDROPHENYLALANINE; GAUCHE ORIENTATION; OPIOID RECEPTOR PHARMACOPHORE; PEPTIDE LIGANDS; TETRAPEPTIDES;

POLYPEPTIDES;

DELTA OPIATE RECEPTOR; DRUG CARRIER; TETRAPEPTIDE; TYROSYLCYCLO[DEXTRO CYSTEINYLPHENYLALANYL DEXTRO PENICILLAMINE];

ARTICLE; CONFORMATIONAL TRANSITION; ENERGY TRANSFER; MOLECULAR DYNAMICS; PROTEIN CONFORMATION; PROTEIN FOLDING; PROTEIN PROTEIN INTERACTION; PROTEIN STABILITY; RECEPTOR AFFINITY;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; ENKEPHALINS; GUINEA PIGS; LIGANDS; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PROTEIN CONFORMATION; RECEPTORS, OPIOID, DELTA; THERMODYNAMICS;

EID: 0030248962     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-0282(199609)39:3<287::aid-bip2>3.0.co;2-k     Document Type: Article

References (26)

1. Mosberg, H. I., Omnaas, J. R., Medzihradsky, F. & Smith, C. B. (1988) Life Sci. 43, 1013-1020.
2. Lomize, A. L., Flippen-Anderson, J. L., George, C. & Mosberg, H. I. (1994) Am. Chem. Soc. 116, 429-436.
3. Mosberg, H. I., Lomize, A. L., Wang, C., Kroona, H., Heyl, D. L., Sobczyk-Kojiro, K., Ma, W., Mousigian, C. & Porreca, F. (1994) J. Med. Chem. 37, 4371-4383.
4. Mosberg, H. I., Omnaas, J. R., Lomize, A. L., Heyl, D. L., Nordan, I., Mousigian, C., Davis, P. & Porreca, F. (1994) J. Med. Chem. 37, 4384-4391.
5. Lomize, A. L., Pogozheva, I. D. & Mosberg, H. I. (1996) Biopolymers, 38, 221-234.
6. Uma, K., Chauhan, V. S., Kumar, A. & Balaram, P. (1988) Peptide Protein Res. 31, 349-358.
7. Pietrzynski, G., Rzeszotarska, B. & Kubica, Z. (1992) Int. J. Peptide Protein Res. 40, 524-531.
8. Aubry, A., Allier, F., Boussard, G. & Marraud, M. (1985) Biopolymers 24, 639-646.
9. Ajo, D., Busetti, V. & Granozzi, G. (1982) Tetrahedron 38, 3329-3334.
10. Ajo, D., Busetti, V., Ottenheijm, H. C. J. & Plate, R. (1984) Acta Crystal. C40, 324-327.
11. Singh, T. P., Haridas, M., Chauhan, V. S., Kumar, A. & Viterbo, D. (1987) Biopolymers 26, 819-829.
12. Glowka, M. L., Gilli, G., Bertolasi, V. & Makowski, M. (1987) Acta Crystal. C43, 1403-1406.
13. Singh, T. P., Narula, P., Chauhan, V. S. & Kaur, P. (1989) Biopolymers 28, 1287-1294.
14. Patel, H. C., Singh, T. P., Chauhan, V. S. & Kaur, P. (1990) Biopolymers 29, 509-515.
15. Aubry, A., Pietrzynski, G., Rzeszotarska, B., Boussard, G. & Marraud, M. (1991) Int. J. Peptide Protein Res. 37, 39-45.
16. Busetti, V., Crisma, M., Toniolo, C., Salvadori, S. & Balboni, G. (1992) Int. J. Biol. Macromol. 14, 23-28.
17. Chauhan, V. S. & Bhandary, K. K. (1992) Int. J. Peptide Protein Res. 39, 223-228.
18. Rajashankar, K. R., Ramakumar, S. & Chauhan, V. S. (1992) J. Am. Chem. Soc. 114, 9225-9226.
19. Bhandary, K. K. & Chauhan, V. S. (1993) Biopolymers 33, 209-217.
20. Rajashankar, K. R., Ramakumar, S., Mal, T. K., Jain, R. M. & Chauhan, V. S. (1994) Biopolymers 35, 141-147.
21. Ciajolo, M. R., Tuzzi, A., Pratesi, C. R., Fissi, A. & Pieroni, O. (1990) Biopolymers 30, 911-920.
22. Momany, F. A. & Rone, R. (1992) J. Comput. Chem. 13, 888-900.
23. Nitz, T. J., Shimohigashi, Y., Costa, T., Chen, H.-C. & Stammer, C. H. (1986) Int. J. Peptide Protein Res. 27, 522-529.
24. Easton, C. J., Hutton, C. A., Roselt, P. D. & Tiekink, E. R. T. (1991) Aust. J. Chem. 44, 687-694.
25. Heyl, D. L. & Mosberg, H. I. (1992) J. Med. Chem. 35, 1535-1541.
26. Munson, P. J. & Rodbard, D. (1980) Anal. Biochem. 107, 220-239.