New Boronic Acid Fluorescent Reporter Compounds. 2. A Naphthalene-Based On-Off Sensor Functional at Physiological pH

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4615-4618

  Gao, Xingming ^a   Zhang, Yanling ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; BUFFER; FRUCTOSE; NAPHTHALENE; PHOSPHATE;

AQUEOUS SOLUTION; ARTICLE; FLUORESCENCE; PH; SENSOR; SYNTHESIS;

1-NAPHTHYLAMINE; BORON; BORONIC ACIDS; CARBOHYDRATES; FLUORESCENCE; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHALENES; SPECTROMETRY, FLUORESCENCE; TITRIMETRY;

EID: 0348042005     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035783i     Document Type: Article

References (38)

1. (a) James, T. D.; Linnane, P.; Shinkai, S. Chem. Commun. 1996, 281-288.
2. (b) Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
3. (c) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155-3184.
4. (d) Wang, W.; Gao, X.; Wang, B. Curr. Org. Chem. 2002, 6, 1285-1317.
5. (a) Yang, W.; Gao, S.; Gao, X.; Karnati, V. R.; Ni, W.; Wang, B.; Hooks, W. B.; Carson, J.; Weston, B. Bioorg. Med. Chem. Lett. 2002, 12, 2175-2177.
6. (b) Yang, W.; Hooks, W. B.; Gao, X.; Gao, S.; Karnati, V. V. R.; Ni, W.; Carson, J.; Weston, B.; Wang, B. Chem. Bio. Submitted for publication.
7. (a) Sugihara, J. M.; Bowman, C. M. J. Am. Chem. Soc. 1958, 80, 2443.
8. (b) Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769.
9. (c) Springsteen, G.; Wang, B. Tetrahedron 2002, 58, 5291-5300.
10. (a) Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874-5875.
11. (b) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Chem. Commun. 1994, 477-478.
12. (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 2207-2209.
13. (d) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature (London) 1995, 374, 345-347.
14. (e) Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem. 1999, 64, 3846-3852.
15. (f) Adhikiri, D. P.; Heagy, M. D. Tetrahedron Lett. 1999, 40, 7893-7896.
16. (g) Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
17. (h) Ward, C. J.; Patel, P.; Ashton, P. R.; James, T. D. Chem. Commun. 2000, 229-230.
18. (i) DiCesare, N.; Lakowicz, J. R. J. Phys. Chem. A 2001, 105, 6834-6840.
19. (j) Yang, W.; He, H.; Drueckhammer, D. G. Angew. Chem., Int. Ed. 2001, 40, 1714-1718.
20. (a) Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 1083-1084.
21. (b) James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982-8987.
22. (a) Wang, W.; Gao, S.; Wang, B. Org. Lett. 1999, 1, 1209-1212.
23. (b) Gao, S.; Wang, W.; Wang, B. Bioorg. Chem. 2001, 29, 308-320.
24. (c) Karnati, V. R.; Gao, X.; Gao, S.; Yang, W.; Ni, W.; Sankar, S.; Wang, B. Bioorg. Med. Chem. Lett. 2002, 12, 3373-3377.
25. (d) Yang, W.; Yan, J.; Fang, H.; Wang, B. Chem. Commun. 2003, 792-793.
26. Yang, W.; Yan, J.; Springsteen, G.; Wang, B. Bioorg. Med. Chem. Lett. 2003, 13, 1019-1022.
27. (a) Arimori, S.; Bosch, L. I.; Ward, C. J.; James, T. D. Tetrahedron Lett. 2001, 42, 4553-4555.
28. (b) DiCesare, N.; Lakowicz, J. R. Chem. Commun. 2001, 2022-2023.
29. (c) DiCesare, N.; Lakowicz, J. R. Anal. Biochem. 2002, 301, 111-116.
30. 2O: C, 71.51, H, 6.25, N, 6.95. Found: C, 71.80, H, 6.42, N, 6.65.
31. Goldman, M.; Wehry, E. L. Anal. Chem. 1970, 42, 1186-1188.
32. -5 M) and the sugar was dissolved in 0.1 M phosphate buffer (pH 7.40) at various concentrations. For fluorescent binding studies, 2 mL of the sensor solution was mixed with 2 mL of the sugar solution. After being stirred for 20 min, the mixture was transferred into a cuvette, and the fluorescence intensity was recorded immediately.
33. (a) Hamai, S. Bull. Chem. Soc. Jpn. 1982, 55, 2721-2729.
34. (b) Sanchez, F. G.; Lopez, M. H.; Gomez, J. C. M. Analyst 1987, 112, 1037-1040.
35. (c) Tong, L. Cyclodextrin Chemistry-Base and Applications; Scientific Publisher: Beijing, China, 2001; pp 145-148.
36. (d) Fery-Forgues, S.; Le Bris, M.-T.; Guetté, J.-P.; Valeur, B. J. Phys. Chem. 1988, 92, 6233-7237.
37. (a) Norrild, J. C.; Eggert, H. J. Chem. Soc., Perkin Trans. 2 1996, 2583-2588.
38. (b) Norrild, J. C. J. Chem. Soc.. Perkin Trans. 2 2001, 719-726.