Comparative study of polyaromatic and polyheteroaromatic fluorescent photocleavable protecting groups

Tetrahedron

Volumn 64, Issue 13, 2008, Pages 3032-3038

  Fernandes, Maria J G ^a   Gonçalves, M Sameiro T ^a   Costa, Susana P G ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Aminobutyric acid (GABA); Coumarin; Oxobenzobenzopyran; Oxobenzopyran; Photocleavable protecting groups

Indexed keywords

4 AMINOBUTYRIC ACID; COUMARIN; ESTER DERIVATIVE; N BENZYLOXYCARBONYL LEVO GAMMA AMINOBUTYRIC ACID (4 METHOXY NAPHTHALEN 1 YL)METHYL ESTER; N BENZYLOXYCARBONYL LEVO GAMMA AMINOBUTYRIC ACID (7 METHOXY 3 OXO 3H BENZO[G]BENZOPYRAN 1 YL)METHYL ESTER; N BENZYLOXYCARBONYL LEVO GAMMA AMINOBUTYRIC ACID (9 METHOXY 3 OXO 3H BENZO[F]BENZOPYRAN 1 YL)METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET IRRADIATION;

EID: 39149086675     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.032     Document Type: Article

References (42)

1. Barltrop J.A., and Schofield P. Tetrahedron Lett. 3 (1962) 697
2. Liu Z.-C., Shin D.-S., Shokouhimehr M., Lee K.-N., Yoo B.-W., Kim Y.-K., and Lee Y.-S. Biosens. Bioelectron. 22 (2007) 2891
3. Gagey N., Neveu P., Benbrahim C., Goetz B., Aujard I., Baudin J.-B., and Jullien L. J. Am. Chem. Soc. 129 (2007) 9986
4. Gagey N., Neveu P., and Jullien L. Angew. Chem., Int. Ed. 46 (2007) 2467
5. Pelliccioli A.P., and Wirz J. Photochem. Photobiol. Sci. 1 (2002) 441
6. Bourgault S., Létourneau M., and Fournier A. Peptides 28 (2007) 1074
7. Adams S.R., Kao J.P.Y., and Tsien R.Y. J. Am. Chem. Soc. 111 (1989) 7957
8. Ellis-Davies G.C.R., and Barsotti R.J. Cell Calcium 39 (2006) 75
9. Maier W., Corrie J.E.T., Papageorgiou G., Laube B., and Grewer C. J. Neurosci. Methods 142 (2005) 1
10. Huang Y.H., Sinha S.R., Fedoryak O.D., Ellis-Davies G.C.R., and Bergles D.E. Biochemistry 44 (2005) 3316
11. Banerjee A., Grewer C., Ramakrishnan L., Jager J., Gameiro A., Breitinger H.-G.A., Gee K.R., Carpenter B.K., and Hess G.P. J. Org. Chem. 68 (2003) 8361
12. Li L.-S., Babendure J.L., Sinha S.C., Olefsky J.M., and Lerner R.A. Bioorg. Med. Chem. Lett. 15 (2005) 3917
13. Schlichting I., Rapp G., John J., Wittinghoffer A., Pai E.F., and Goody R.S. Proc. Natl. Acad. Sci. U.S.A. 86 (1989) 7687
14. Aujard I., Benbrahim C., Gouget M., Ruel O., Baudin J.-B., Neveu P., and Jullien L. Chem.-Eur. J. 12 (2006) 6865
15. Pincock J.A. Acc. Chem. Res. 30 (1997) 43
16. Cameron J.F., Willson C.G., and Fréchet J.M.J. J. Am. Chem. Soc. 118 (1996) 12925
17. Givens R.S., Weber J.F.W., Conrad P.G., Orosz G., Donahue S.L., and Thayer S.A. J. Am. Chem. Soc. 122 (2000) 2687
18. Turner A.D., Pizzo S.V., Rozakis G.W., and Porter N.A. J. Am. Chem. Soc. 109 (1987) 1274
19. Pirrung M.C., Fallon L., Zhu J., and Lee Y.R. J. Am. Chem. Soc. 123 (2001) 3638
20. Furuta T., Hirayama Y., and Iwamura M. Org. Lett. 3 (2001) 1809
21. Yu J.-Y., Tang W.-J., Wang H.-B., and Song Q.-H. J. Photochem. Photobiol., A 185 (2007) 101
22. Iwamura M., Hodota C., and Ishibashi M. Synlett (1991) 35
23. Iwamura M., Ishikawa T., Koyama Y., Sakuma K., and Iwamura H. Tetrahedron Lett. 28 (1987) 679
24. Singh A.K., and Prashant K.K. Tetrahedron Lett. 46 (2005) 5563
25. Shembekar V.R., Chen Y., Carpenter B.K., and Hess G.P. Biochemistry 44 (2005) 7107
26. Hagen V., Bendig J., Frings S., Wiesner B., Schade B., Helm S., Lorenz D., and Kaupp U.B. J. Photochem. Photobiol., B: Biol. 53 (1999) 91
27. Muller C., Even P., Viriot M.-L., and Carré M.-C. Helv. Chim. Acta 84 (2001) 3735
28. Tang X.J., and Dmochowski I.J. Org. Lett. 7 (2005) 279
29. Vasquez M.E., Nitz M., Stehn J., Yaffe M.B., and Imperiali B. J. Am. Chem. Soc. 125 (2003) 10150
30. Canepari M., Nelson L., Papageorgiou G., Corrie J.E.T., and Ogden D. J. Neurosci. Methods 112 (2001) 29
31. Curten B., Kullmann H.M.P., Bier M.E., Kandler K., and Schmidt B.F. Photochem. Photobiol. 81 (2005) 641
32. Piloto A.M., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron Lett. 46 (2005) 4757
33. Piloto A.M., Fonseca A.S.C., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron 62 (2006) 9258
34. Piloto A.M., Rovira D., Costa S.P.G., and Gonçalves M.S.T. Tetrahedron 62 (2006) 11955
35. Fonseca A.S.C., Gonçalves M.S.T., and Costa S.P.G. Tetrahedron 63 (2007) 1353
36. Fernandes M.J.G., Gonçalves M.S.T., and Costa S.P.G. Tetrahedron 63 (2007) 10133
37. Tao Z.-F., Qian X., and Fan M. Tetrahedron 53 (1997) 13329
38. Buchi G., Foulkes D.M., Kurono M., Mitchell G.F., and Schneider R.S. J. Am. Chem. Soc. 89 (1967) 6745
39. Furuta T., Takeuchi H., Isozaki M., Takahashi Y., Kahenara M., Sugimoto M., Watanabe T., Noguchi K., Dore T.M., Kurahashi T., Iwamura M., and Tsien R.Y. ChemBioChem 5 (2004) 1119
40. Bodanszky M., and Bodanszky A. The Practice of Peptide Synthesis (1984), Springer, Berlin
41. Tjoeng F.S., and Heavner G.A. Synthesis (1981) 897
42. Morris J.V., Mahaney M.A., and Huber J.R. J. Phys. Chem. 80 (1976) 969