Desyl esters of amino acid neurotransmitters. Phototriggers for biologically active neurotransmitters

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1228-1233

  Gee, Kyle R ^a   Kueper III, L William ^b   Barnes, Jeffrey ^b   Dudley, Gregory ^b   Givens, Richard S ^b  

^a MOLECULAR PROBES INC   (United States)

^b UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; GLUTAMATE RECEPTOR; GLUTAMIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; BRAIN; CONTROLLED STUDY; DRUG SYNTHESIS; FERRET; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NERVE CELL; NONHUMAN; PHOTOCHEMISTRY;

EID: 0029865909     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951635x     Document Type: Article

References (34)

1. (a) Givens, R. S.; Athey, P. S.; Kueper, L. W., III; Matuszewski, B.; Xue, J.-y, J. Am. Chem. Soc. 1992, 114, 8708.
2. (b) Givens, R. S.; Athey, P. S.; Kueper, L. W., III; Matuszewski, B ; Xue, J.-y.; Fister, T. J. Am. Chem. Soc. 1993, 115, 6001.
3. Corrie, J. E. T.; Reid, D. R.; Trentham, M. B.; Mazid, M. A. J. Chem Soc., Perkin Trans. 1 1992, 1015.
4. (a) Adams, S. R.; Tsien, R. Y. Ann. Rev. Physiol. 1993, 55, 755-783.
5. (b) Corrie, J. E. T.; Trentham, D. R. In Bioorganic Photochemistry; Morrison, H., Ed.; Wiley: New York, 1993; Vol. 2, pp 243-305.
6. (c) Hess, G. P. Biochemistry 1993, 32, 989-1000.
7. (d) Givens, R. S.; Kueper, L. W., III. Chem. Rev. 1993, 93, 55-66.
8. Patchornik, A.; Amit, B.; Woodward, R. B. J. Am. Chem. Soc. 1970, 92, 6333-6335.
9. Kaplan, J. H.; Forbush, G., III; Huffman, J. F. Biochemistry 1978, 17, 1929.
10. (a) Corrie, J. E. T.; Trentham, D. R. J. Chem. Soc., Perkin Trans. 1 1992, 2409-2417.
11. (b) Thirlwell, H.; Corrie, J. E. T.; Reid, G. P.; Trentham, D. R.; Ferenczi, M. A. Biophys. J. 1994, 67, 2436.
12. (a) Sheehan, J. C.; Wilson, R. M. J. Am. Chem. Soc. 1964, 86, 5277-5281.
13. (b) Sheehan, J. C., Wilson, R. M.; Oxford, A. W. J. Am. Chem. Soc. 1971, 93, 7222-7228.
14. (c) Sheehan, J. C.; Umezawa, J. J. Org. Chem. 1973, 38, 3771-3774.
15. Givens, R. S.; Matuszewski, B. J. Am. Chem. Soc. 1984, 106, 6860.
16. Baldwin, J. E ; MeConnaughie, A. W.; Moloney, M. G.; Pratt, A. J.; Shim, S. B. Tetrahedron 1990, 46, 6879-6884.
17. Pirrung, M. C.; Shuey, S. W. J. Org. Chem. 1994, 59, 3890-3897.
18. (a) Futura, T.; Torigai, H.; Sugimoto, M; Iwamura, M. J. Org Chem. 1995, 60, 3953-3956.
19. (b) Futura, T.; Torigai, H.; Osawa, T.; Iwamura, M. Chem. Lett. 1993, 1179-1182.
20. Cameron, J. F.; Willson, C. G.; Fréchet, J. M. J. J. Chem. Soc., Chem. Commun 1995, 923-924.
21. (a) Wieboldt, R.; Gee, K. R.; Nui, L.; Ramesh, D.; Carpenter, B. K.; Hess, G. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 8752-8756.
22. (b) Gee, K. R.; Wieboldt, R.; Hess, G. P. J. Am. Chem. Soc. 1994, 116, 8366-8367.
23. A preliminary account of these results was presented at the 208th National Meeting of the American Chemical Society, Organic Division, Washington, DC, August 22-26, 1994, Abstract #351.
24. (a) Dalva, M. B.; Katz, L. C. Science 1994, 265, 255-258.
25. (b) Callaway, E. M.; Katz, L. C. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7661-7665.
26. (c) Katz, L. C.; Dalva, M C. J. Neurosci. Methods 1994, 54, 205-218.
27. Church, G, Ferland, J.-M.; Gauthier, J. Tetrahedron Lett. 1989, 30, 1901.
28. 19
29. (a) Decosta, D. P.; Pincock, J. A. J. Am. Chem. Soc. 1993, 115, 2180.
30. (b) Hilborn, J. W.; MacKnight, E.; Pincock, J. A.; Wedge, P J. J. Am. Chem. Soc. 1994, 116, 3337.
31. (c) Kim, J. M.; Pincock, J. A. Can. J. Chem. 1995, 73, 885-895.
32. Givens, R. S.; Matuszewski, B.; Athey, P. S.; Stoner, R. J. Am. Chem. Soc. 1990, 112, 6016 and references therein.
33. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
34. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London, Ser. 4 1956, 235, 518-526.