A new type of boronic acid fluorescent reporter compound for sugar recognition

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 7981-7984

  Yang, Wenqian ^a   Lin, Li ^a   Wang, Binghe ^a,b  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Boronic acid; Fluorescent; Heterocycles; pKa; Quinoline; Sensing; Sensor; Sugar recognition

Indexed keywords

5 QUINOLINEBORONIC ACID; BORONIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; DRUG STRUCTURE; FLUORESCENCE;

EID: 26844529312     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.074     Document Type: Article

References (53)

1. M. Fukuda, and O. Hindsgaul Molecular Glycobiology 1994 Oxford University Press New York pp 1-52
2. A. Alavi, and J.S. Axford Glycoimmunology Adv. Exp. Med. Biol. Vol. 376 1995 Plenum Press New York
3. S. Brodesser, P. Sawatzki, and T. Kolter Euro. J. Org. Chem. 11 2003 2021 2034
4. H.-J. Gabius, and S. Gabius Lectins and Glycobiology 1993 Springer New York
5. A. Danguy, I. Camby, and R. Kiss Biochem. Biophys. Acta-Gen. Subj. 1572 2002 285 293
6. N. Bidon-Wagner, and J.P. Le Pennec Glycoconjug. J. 19 2004 557 563
7. For general references on various factors that affect the binding affinity and boronic acid-based sensor design, see: J.P. Lorand, and J.O. Edwards J. Org. Chem. 24 1959 769
8. G. Springsteen, and B. Wang Tetrahedron 58 2002 5291 5300
9. J. Yan, G. Springsteen, S. Deeter, and B. Wang Tetrahedron 60 2004 11205 11209
10. H. Fang, J. Yan, and B. Wang Med. Res. Rev. 25 2005 490 520
11. For reviews, see: T.D. James, and S. Shinkai Top. Curr. Chem. 218 2002 159 200
12. S.L. Wiskur, J.J. Lavigne, A. Metzger, S.L. Tobey, V. Lynch, and E.V. Anslyn Chem.-A Eur. J. 10 2004 3792 3804
13. J.H. Hartley, T.D. James, and C.J. Ward J. Chem. Soc., Perkin Trans. 1 2000 3155 3184
14. W. Wang, X. Gao, and B. Wang Curr. Org. Chem. 6 2002 1285 1317
15. W. Yang, X. Gao, and B. Wang Med. Res. Rev. 23 2003 346 368
16. S. Striegler Curr. Org. Chem. 7 2003 81 102
17. H.S. Cao, and M.D. Heagy J. Fluorescence 14 2004 569 584
18. W. Yang, S. Gao, and B. Wang D. Hall Organoboronic Acids 2005 John Wiley and Sons New York 481 512
19. S. Shinkai, and M. Takeuchi Trends Anal. Chem. 15 1996 188 193
20. For examples see: J. Yoon, and A.W. Czarnik J. Am. Chem. Soc. 114 1992 5874 5875
21. T.D. James, K.R.A.S. Sandanayake, and S. Shinkai Chem. Commun. 1994 477 478
22. E. Eggert, J. Frederiksen, C. Morin, and J.C. Norrild J. Org. Chem. 64 1999 3846 3852
23. W. Yang, J. Yan, H. Fang, and B. Wang Chem. Commun. 2003 792 793
24. W. Wang, S. Gao, and B. Wang Org. Lett. 1 1999 1209 1212
25. W. Yang, H. He, and D.G. Drueckhammer Angew. Chem., Int. Ed. 40 2001 1714 1718
26. H. Cao, D.I. Diaz, D. DiCesare, J.R. Lakowicz, and M.D. Heagy Org. Lett. 4 2002 1503 1506
27. N. DiCesare, and J.R. Lakowicz Anal. Biochem. 294 2001 154 160
28. C.J. Ward, P. Patel, P.R. Ashton, and T.D. James Chem. Commun. 2000 229 230
29. V.L. Alexeev, A.C. Sharma, A.V. Goponenko, S. Das, I.K. Lednev, C.S. Wilcox, D.N. Finegold, and S.A. Asher Anal. Chem. 75 2003 2316 2323
30. C.J. Davis, P.T. Lewis, M.E. McCarroll, M.W. Read, R. Cueto, and R.M. Strongin Org. Lett. 1 1999 331 334
31. P.R. Westmark, S.J. Gardiner, and B.D. Smith J. Am. Chem. Soc. 118 1996 11093 11100
32. S.P. Draffin, P.J. Duggan, and S.A.M. Duggan Org. Lett. 3 2001 917 920
33. J.J. Lavigne, and E.V. Anslyn Angew. Chem., Int. Ed. 38 1999 3666 3669
34. D. Stones, S. Manku, X. Lu, and D.G. Hall Chem. Eur. J. 10 2004 92 100
35. A.M. Irving, C.M. Vogels, L.G. Nikolcheva, J.P. Edwards, X.F. He, M.G. Hamilton, M.O. Baerlocher, F.J. Baerlocher, A. Decken, and S.A. Westcott New J. Chem. 27 2003 1419 1424
36. H.R. Mulla, N.J. Agard, and A. Basu Bioorg. Med. Chem. Lett. 14 2004 25 27
37. V.R.R. Karnati, X. Gao, S. Gao, W. Yang, W. Ni, and B. Wang Bioorg. Med. Chem. Lett. 12 2002 3373 3377
38. O. Rusin, O. Alpturk, M. He, J.O. Escobedo, S. Jiang, F. Dawan, K. Lian, M.E. McCarroll, I.M. Warner, and R.M. Strongin J. Fluorescence 14 2004 611 615
39. K.L. Kramp, K. DeWitt, J.W. Flora, D.C. Muddiman, K.M. Slunt, and T.A. Houston Tetrahedron Lett. 46 2005 695 698
40. W. Yang, H. Fan, S. Gao, X. Gao, W. Ni, V. Karnati, W.B. Hooks, J. Carson, B. Weston, and B. Wang Chem. Biol. 11 2004 439 448
41. W. Yang, S. Gao, X. Gao, V.V.R. Karnati, W. Ni, B. Wang, W.B. Hooks, J. Carson, and B. Weston Bioorg. Med. Chem. Lett. 12 2002 2175
42. T.J. Burnett, H.C. Peebles, and J.H. Hageman Biochem. Biophy. Res. Comm. 96 1980 157 162
43. S. Patterson, B.D. Smith, and R.E. Taylor Tetrahedron Lett. 39 1998 3111 3114
44. Z.Y. Zhang, and B.D. Smith J. Am. Chem. Soc. 120 1998 7141 7142
45. K.L. Kramp, K. DeWitt, J.W. Flora, D.C. Muddiman, K.M. Slunt, and T.A. Houston Tetrahedron Lett. 46 2005 695 698
46. X. Gao, Y. Zhang, and B. Wang Tetrahedron 61 2005 9111 9117
47. W. Yang, G. Springsteen, J. Yan, S. Deeter, and B. Wang Bioorg. Med. Chem. Lett. 13 2003 1019 1022
48. X. Gao, Y. Zhang, and B. Wang Org. Lett. 5 2003 4615 4618
49. W. Yang, L. Lin, and B. Wang Heterocycl. Commun. 10 2004 383 388
50. R.G. Bates Determination of pH 1964 John Wiley & Sons, Inc. London
51. S.L. Wiskur, J.L. Lavigne, H. Ait-Haddou, V. Lynch, Y.H. Chiu, J.W. Canary, and E.V. Anslyn Org. Lett. 3 2001 1311 1314
52. See Ref. 5b. W. Ni, G. Kaur, G. Springsteen, B. Wang, and S. Franzen Bioorg. Chem. 2004 32
53. S. Franzen, W. Ni, and B. Wang J. Phys. Chem. B 107 2003 12942 12948