The relationship among pK a, pH, and binding constants in the interactions between boronic acids and diols - It is not as simple as it appears

Tetrahedron

Volumn 60, Issue 49, 2004, Pages 11205-11209

  Yan, Jun ^a   Springsteen, Greg ^a   Deeter, Susan ^a   Wang, Binghe ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Binding constants; Boronic acids; pH; pK a

Indexed keywords

BORONIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BINDING AFFINITY; CELL SURFACE; CHEMICAL REACTION; COMPLEX FORMATION; MOLECULAR INTERACTION; PH MEASUREMENT; PKA; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 7044263179     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.08.051     Document Type: Article

References (43)

1. G. Springsteen, and B. Wang Tetrahedron 58 2002 5291 5300
2. G. Springsteen, and B. Wang Chem. Commun. 2001 1608 1609
3. T.D. James, K.R.A.S. Sandanayake, R. Iguchi, and S. Shinkai J. Am. Chem. Soc. 117 1995 8982 8987
4. H. Eggert, J. Frederiksen, C. Morin, and J.C. Norrild J. Org. Chem. 64 1999 3846 3852
5. T.D. James, K.R.A.S. Sandanayake, and S. Shinkai Angew. Chem. Int. Ed. Engl. 35 1996 1910 1922
6. W. Wang, S. Gao, and B. Wang Org. Lett. 1 1999 1209 1212
7. J. Yoon, and A.W. Czarnik J. Am. Chem. Soc. 114 1992 5874 5875
8. D.P. Adhikiri, and M.D. Heagy Tetrahedron Lett. 40 1999 7893 7896
9. S. Arimori, L.I. Bosch, C.J. Ward, and T.D. James Tetrahedron Lett. 42 2001 4553 4555
10. L.A. Cabell, M.-K. Monahan, and E.V. Anslyn Tetrahedron Lett. 40 1999 7753 7756
11. W. Yang, H. He, and D.G. Drueckhammer Angew. Chem. Int. Ed. 40 2001 1714 1718
12. W. Wang, X. Gao, and B. Wang Curr. Org. Chem. 6 2002 1285 1317
13. W. Yang, J. Yan, G. Springsteen, S. Deeter, and B. Wang Bioorg. Med. Chem. Lett. 13 6 2003 1019 1022
14. S.P. Draffin, P.J. Duggan, and S.A.M. Duggan Org. Lett. 3 2001 917 920
15. S. Gardiner, B. Smith, P. Duggan, M. Karpa, and G. Griffin Tetrahedron 55 1999 2857 2864
16. M. Karpa, P. Duggan, G. Griffin, and S. Freudigmann Tetrahedron 53 1997 3669 3678
17. L.K. Mohler, and A.W. Czarnik J. Am. Chem. Soc. 115 1993 2998 2999
18. M.-F. Paugam, J.T. Bien, B.D. Smith, L.A.J. Chrisstoffels, F. de Jong, and D.N. Reinhoudt J. Am. Chem. Soc. 118 1996 9820 9825
19. J.A. Riggs, K.A. Hossler, B.D. Smith, M.J. Karpa, G. Griffin, and P.J. Duggan Tetrahedron Lett. 37 1996 6303 6306
20. B.D. Smith, S.J. Gardiner, T.A. Munro, M.F. Paugam, and J.A. Riggs J. Incl. Phenom. Mol. Recogn. Chem. 32 1998 121 131
21. P.R. Westmark, S.J. Gardiner, and B. Smith J. Am. Chem. Soc. 118 1996 11093 11100
22. V. Adamek, X.-C. Liu, Y.A. Zhang, K. Adamkova, and W.H. Scouten J. Chromatogr. 625 1992 91 99
23. A. Bergold, and W.H. Scouten Chem. Anal. (NY) 66 1983 149 187
24. V. Bouriotis, J. Galpin, and P.D.G. Dean J. Chromatogr. 210 1981 267 268
25. X. Liu, J. Hubbard, and W. Scouten J. Organomet. Chem. 493 1995 91 94
26. J. Psotova, and O. Janiczek Chem. Listy 89 1995 641 648
27. H. Seliger, and V. Genrich Experientia 30 1974 1480 1481
28. R. Singhal, and S. DeSilva J. Giddings E. Grushka P. Brown Advanced Chromatography Vol. 31 1992 Marcel Dekker New York 293 335
29. P.R. Westmark, L.S. Valencia, and B.D. Smith J. Chromatogr. A 664 1994 123 128
30. A. Sugasaki, K. Sugiyasu, M. Ikeda, M. Takeuchi, and S. Shinkai J. A.m. Chem. Soc. 123 2001 10239 10244
31. W. Yang, S. Gao, X. Gao, V.R. Karnati, W. Ni, B. Wang, W.B. Hooks, J. Carson, and B. Weston Bioorg. Med. Chem. Lett. 12 2002 2175 2177
32. W. Yang, X. Gao, and B. Wang Med. Res. Rev. 23 2003 346 368
33. H.R. Mulla, N.J. Agard, and A. Basu Bioorg. Med. Chem. Lett. 14 2003 25 27
34. S. Soundararajan, M. Badawi, C.M. Kohlrust, and J.H. Hageman Anal. Biochem. 178 1989 125 134
35. H. Corwin, A. Leo, and R.W. Taft Chem. Rev. 91 1991 165 195
36. T.D. James, P. Linnane, and S. Shinkai Chem. Commun. 1996 281 288
37. M. Van Duin, J.A. Peters, A.P.G. Kieboom, and H. Van Bekkum Tetrahedron 40 1984 2901 2911
38. X. Liu, and W. Scouten J. Chromatogr. A 687 1994 61 69
39. R.P. Singhal, B. Ramamurthy, N. Govindraj, and Y. Sarwar J. Chromatogr. 543 1991 17 38
40. P.A. Sienkiewicz, and D.C.J. Roberts Inorg. Nucl. Chem. 42 11 1980 1559 1575
41. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants, 3rd ed.; London: Chapman and Hall, 1984.
42. H.R. Mulla, N.J. Agard, and A. Basu Bioorg. Med. Chem. Lett. 14 2004 25 27
43. M. Bielecki, H. Eggert, and J.C. Norrild J. Chem. Soc., Perkin Trans. 2 3 1999 449 456