The design, synthesis, and initial evaluation of benzophenone-containing peptides as potential photoaffinity labels of oligosaccharyltransferase

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 10, 1998, Pages 1821-1834

  Xu, Tong ^a   Khanna, Hemant ^a   Coward, James K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Benzophenone; Oligosaccharyltransferase; Photoaffinity label; Photophore

Indexed keywords

BENZOPHENONE DERIVATIVE; OLIGOSACCHARYLTRANSFERASE; TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; DRUG DESIGN; DRUG SYNTHESIS; ENZYME SUBSTRATE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOAFFINITY LABELING; PROTEIN GLYCOSYLATION;

BENZOPHENONES; HEXOSYLTRANSFERASES; MEMBRANE PROTEINS; PEPTIDES; PHOTOAFFINITY LABELS; TRANSFERASES;

EID: 0031725908     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00135-7     Document Type: Article

References (29)

1. Imperiali, B.; Hendrickson, T. L. Bioorg. Med. Chem. 1995, 3, 1565.
2. Silberstein, S.; Gilmore, R. FASEB J. 1996, 10, 849.
3. Marshall, R. D. Ann. Rev. Biochem. 1972, 41, 673.
4. Gavel, Y.; von Heijne, G. Prot. Eng. 1990, 3, 433.
5. Bause, E.; Legler, G. Biochem. J. 1981, 195, 639.
6. Imperiali, B.; Shannon, K. L.; Unno, M.; Rickert, K. W. J. Am. Chem. Soc. 1992, 114, 7944.
7. Clark, R. S.; Banerjee, S.; Coward, J. K. J. Org. Chem. 1990, 55, 6275.
8. Lee, J.; Coward, J. K. Biochemistry 1993, 32, 6794.
9. Xu, T.; Coward, J. K. Biochemistry 1997, 36, 14683.
10. Pathak, R.; Hendrickson, T. L.; Imperiali, B. Biochemistry 1995, 34, 4179.
11. Xu, T.; Werner, R. M.; Lee, K.-C.; Fettinger, J. C.; Davis, J. T.; Coward, J. K. J. Org. Chem. 1998, 63, 4767.
12. Bause, E. Biochem J. 1983, 209, 323.
13. Bause, E.; Wesemann, M.; Bartoschek, A.; Breuer, W. Biochem J. 1997, 322, 95.
14. Welply, J. K.; Shenbagamurthi, P.; Naider, F.; Park, H. R.; Lennarz, W. J. J. Biol. Chem. 1985, 260, 6459.
15. Welply, J. K.; Kaplan, H. A.; Shenbagamurthi, P.; Naider, F.; Lennarz, W. J. Arch. Biochem. Biophys. 1986, 246, 808.
16. Kaplan, H. A.; Naider, F.; Lennarz, W. J. J. Biol. Chem. 1988, 263, 7814.
17. Geetha-Habib, M.; Noiva, R.; Kaplan, H. A.; Lennarz, W. J. Cell 1988, 54, 1053.
18. LaMantia, M. L.; Miura, T.; Tachikawa, H.; Kaplan, H. A.; Lennarz, W. J.; Mizunaga, T. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 4453.
19. Dormán, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661.
20. Bernardi, L.; de Castiglione, R.; Fregnan, G. B.; Glässer, A. H. J. Pharm. Pharmacol. 1967, 19, 95.
21. Nakamoto, C.; Behar, V.; Chin, K. R.; Adams, A. E.; Suva, L. J.; Rosenblatt, M.; Chorev, M. Biochemistry 1995, 34, 10546.
22. Bodanszky, M. In The Practice of Peptide Synthesis; Springer-Verlag: 1984; p 66.
23. Ledger, R.; Stewart, F. H. C. Aust. J. Chem. 1965, 18, 933.
24. Forsch, R. A.; Rosowsky, A. J. Org. Chem. 1984, 49, 1305.
25. Cuenoud, B.; Schepartz, A. Tetrahedron 1991, 47, 2535.
26. Lee, J.; Coward, J. K. J. Org. Chem. 1992, 57, 4126.
27. Fang, X.; Gibbs, B. S.; Coward, J. K. Bioorg. Med. Chem. Lett. 1995, 5, 2701.
28. Dixon, M. Biochem. J. 1953, 55, 170.
29. Lee, Y. C. Anal. Biochem. 1990, 189, 151.