Unnatural benz-X-azolyl asparagine derivatives as novel fluorescent amino acids: synthesis and photophysical characterization

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9373-9377

  Esteves, Cátia I C ^a   Silva, Ana M F ^a   Raposo, M Manuela M ^a   Costa, Susana P G ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Asparagine; Benzimidazole; Benzothiazole; Fluorescent probes; Solvatochromism; Unnatural amino acids

Indexed keywords

ASPARAGINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; N TERT BUTYLOXYCARBONYL(6 ETHOXYBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 FLUOROBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 METHOXYBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 METHYLBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 NITROBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 SULFOMETHYLBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(6 THIOCYANOBENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(BENZIMIDAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(BENZOTHIAZOL 2 YL)ASPARAGINE BENZYL ESTER; N TERT BUTYLOXYCARBONYL(BENZOTHIAZOL 6 YL)ASPARAGINE BENZYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE ANALYSIS; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD;

EID: 70349761377     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.086     Document Type: Article

References (37)

1. Watanabe T., Miyata Y., Abe R., Muranaka N., and Hohsaka T. ChemBioChem 9 (2008) 1235-1242
2. Kajihara D., Abe R., Iijima I., Komiyama C., Sissido M., and Hohsaka T. Nat. Methods 3 (2006) 923-929
3. Sahoo H., Hennig A., and Nau W.M. Int. J. Photoenergy (2006) article no. 89638
4. Hennig A., Florea M., Roth D., Enderle T., and Nau W.M. Anal. Biochem. 360 (2007) 255-265
5. Taki M., Hohsaka T., Murakami H., Taira K., and Sisido M. FEBS Lett. 507 (2001) 35-38
6. Cheng R.P., Fisher S.L., and Imperiali B. J. Am. Chem. Soc. 118 (1996) 11349-11356
7. Budisa N., Alefelder S., Bae J.H., Golbik R., Minks C., Huber R., and Moroder L. Protein Sci. 10 (2001) 1281-1292
8. Li B.S., Cheuk K.K.L., Ling L., Chen J., Xiao X., Bai C., and Tang B.Z. Macromolecules 36 (2003) 77-85
9. Ishida H., Kyakuno M., and Oishi S. Biopolymers (Pep. Sci.) 76 (2004) 69-82
10. Hodgson D.R.W., and Sanderson J.M. Chem. Soc. Rev. 33 (2004) 422-430
11. Zeng D.X., and Chen Y. J. Photochem. Photobiol., A 186 (2007) 121-124
12. Shi H.-B., Ji S.-J., and Bian B. Dyes Pigm. 73 (2007) 394-396
13. Moon K.S., Singh N., Lee G.W., and Jang D.O. Tetrahedron 63 (2007) 9106-9111
14. Greco G., Panzella G.L., Napolitano A., and d'Ischia M. Tetrahedron Lett. 50 (2009) 3095-3097
15. Chen L., Cui Y., Qian G., and Wang M. Dyes Pigm. 73 (2007) 338-343
16. Rodembusch F.S., Buckup T., Segala M., Tavares L., Correia R.R.B., and Stefani V. Chem. Phys. 305 (2004) 115-121
17. Yoshida M., Hayakawa I., Hayashi N., Agatsuma T., Oda Y., Tanzawa F., Iwasaki S., Koyama K., Furukawa H., Kurakatad S., and Suganob Y. Bioorg. Med. Chem. Lett. 15 (2005) 3328-3332
18. Costa S.P.G., Maia H.L.S., and Pereira-Lima S.M.M.A. Org. Biomol. Chem. 1 (2003) 1475-1479
19. Jiang W.-Q., Costa S.P.G., and Maia H.L.S. Org. Biomol. Chem. 1 (2003) 3804-3810
20. Costa S.P.G., Oliveira E., Lodeiro C., and Raposo M.M.M. Tetrahedron Lett. 49 (2008) 5258-5261
21. Costa S.P.G., Batista R.M.F., and Raposo M.M.M. Tetrahedron 64 (2008) 9733-9737
22. Batista R.M.F., Costa S.P.G., and Raposo M.M.M. Tetrahedron Lett. 45 (2004) 2825-2828
23. Costa S.P.G., Batista R.M.F., Sousa A.M.R.C., and Raposo M.M.M. Mater. Sci. Forum 514-516 (2006) 147-151
24. Costa S.P.G., Batista R.M.F., Cardoso P., Belsey M., and Raposo M.M.M. Eur. J. Org. Chem. 17 (2006) 3938-3946
25. Batista R.M.F., Costa S.P.G., Malheiro E.L., Belsey M., and Raposo M.M.M. Tetrahedron 63 (2007) 4258-4265
26. Batista R.M.F., Costa S.P.G., Belsley M., and Raposo M.M.M. Tetrahedron 63 (2007) 9842-9849
27. Pina J., Seixas de Melo J., Burrows H.D., Batista R.M.F., Costa S.P.G., and Raposo M.M.M. J. Phys. Chem. A 111 (2007) 8574-8578
28. Batista R.M.F., Costa S.P.G., Belsley M., Lodeiro C., and Raposo M.M.M. Tetrahedron 64 (2008) 9230-9238
29. Batista R.M.F., Costa S.P.G., Belsley M., and Raposo M.M.M. Dyes Pigm. 80 (2009) 329-336
30. Batista R.M.F., Oliveira E., Costa S.P.G., Lodeiro C., and Raposo M.M.M. Org. Lett. 9 (2007) 3201-3204
31. Costa S.P.G., Oliveira E., Lodeiro C., and Raposo M.M.M. Sensors 7 (2007) 2096-2114
32. Batista R.M.F., Oliveira E., Nuñez C., Costa S.P.G., Lodeiro C., and Raposo M.M.M. J. Phys. Org. Chem. 22 (2009) 362-366
33. Holler M.G., Campo L.F., Brandelli A., and Stefani V. J. Photochem. Photobiol., A: Chem. 149 (2002) 217-225
34. Morris J.V., Mahaney M.A., and Huber J.R. J. Phys. Chem. 80 (1976) 969-974
35. Dey J.K., and Dogra S.K. Chem. Phys. 143 (1990) 97-107
36. Dey J.K., and Dogra S.K. Bull. Chem. Soc. Jpn. 64 (1991) 3142-3152
37. Dey J.K., and Dogra S.K. J. Phys. Chem. 98 (1994) 3638-3644 and references therein