Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH

Journal of the American Chemical Society

Volumn 125, Issue 12, 2003, Pages 3493-3502

  Otsuka, Hidenori ^a,d   Uchimura, Eiichiro ^a   Koshino, Hiroyuki ^b   Okano, Teruo ^c   Kataoka, Kazunori ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b RIKEN   (Japan)

^c TOKYO WOMEN'S MEDICAL UNIVERSITY   (Japan)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BONDING; BORON COMPOUNDS; COORDINATION REACTIONS; GLUCOSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC ACIDS; PH; SOLUTIONS; SURFACES;

MOIETIES;

BIOLOGICAL MEMBRANES;

3 (PROPIONAMIDO)PHENYLBORONIC ACID; BENZENEBORONIC ACID; BORIC ACID; BORONIC ACID DERIVATIVE; GALACTOSE; GANGLIOSIDE; GLUCOSE; GLYCOLIPID; GLYCOPROTEIN; MANNOSE; N ACETYLNEURAMINIC ACID; PHENYL GROUP; SIALIC ACID; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; EQUILIBRIUM CONSTANT; MEMBRANE BINDING; NONHUMAN; PH; PKA; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

BORONIC ACIDS; GALACTOSE; GLUCOSE; HYDROGEN-ION CONCENTRATION; KINETICS; MANNOSE; MOLECULAR CONFORMATION; N-ACETYLNEURAMINIC ACID; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SOLUTIONS; WATER;

EID: 0037467441     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021303r     Document Type: Article

References (81)

1. Kitano, S.; Kataoka, K.; Koyama, Y.; Okano, T.; Sakurai, Y. Makromol. Chem., Rapid Commun. 1991, 12, 227.
2. Miyazaki, H.; Okano, T.; Sakurai, Y.; Kataoka, K. Biochem. Biophys. Res. Commun. 1993, 195 (2), 829.
3. Kataoka, K.; Miyazaki, H. Macromolecules 1994, 27, 1061.
4. Aoki, T.; Nagano, Y.; Sanui, K.; Ogata, N.; Kikuchi, A.; Sakurai, Y.; Kataoka, K.; Okano, T. J. Biomater. Sci., Polymer Ed. 1997, 9 (3), 1.
5. Kataoka, K.; Miyazaki, H.; Bunya, M.; Okano, T.; Sakurai, Y. J. Am. Chem. Soc. 1998, 120, 12694.
6. Schott, H.; Rudloff, E.; Schmidt, P.; Roychoudhury, R.; Kossel, H. Biochemistry 1973, 12, 932.
7. Weith, H. L.; Weibers, J. L.; Gilham, P. T. Biochemistry 1970, 9, 4396.
8. Yoshimura, K.; Miyazaki, Y.; Sawada, S.; Waki, H. J. Chem. Soc., Faraday Trans. 1996, 92 (4), 651.
9. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910.
10. Wulff, G.; Vesper, W. J. Chromatogr. 1978, 167, 171.
11. Burgemeister, T.; Grobe-Einsler, R.; Grotstollen, R.; Mannschreck, A.; Wulff, G. Chem. Ber. 1981, 114, 3403.
12. Shinbo, T.; Nhishimura, K.; Yamaguchi, T.; Sugiura, M. J. Chem. Soc., Chem. Commun. 1986, 349.
13. Morin, G. T.; Hughes, M. P.; Paugam, M.-F.; Smith, B. D. J. Am. Chem. Soc. 1994, 116, 8895.
14. Westmark, P. R.; Gardiner, S. J.; Smith, B. D. J. Am. Chem. Soc. 1996, 118, 11093.
15. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910.
16. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345.
17. James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982.
18. Pan, X. Q.; Wang, H.; Shukla, S.; Sekido, M.; Adams, D. M.; Tjarks, W.; Barth, R. F.; Lee, R. J. Bioconjugate Chem. 2002, 13 (3), 435.
19. Stiriba, S.-E.; Frey, H.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 1329.
20. Gallop, P. M.; Paz, M. A.; Henmson, E. Science 1982, 217, 166.
21. (a) Lawler, A. Science 1995, 267, 956.
22. (b) Flam, F. Science 1994, 265, 468.
23. (c) Anderson, C. Science 1993, 262, 329.
24. Hawthore, M. F. Angew. Chem., Int. Ed. Engl. 1993, 32, 950.
25. Barth, R. F.; Yang, W.; Rotaru, J. H.; Moeschberger, M. L.; Joel, D. D.; Nawrocky, M. M.; Goodman, J. H.; Soloway, A. H. Cancer Res. 1997, 57, 1129.
26. Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F.-G.; Barth, R. F.; Codogni, I. M.; Wilson, G. Chem. Rev. 1998, 98, 1515.
27. Nakanishi, A.; Guan, L.; Kane, R. R.; Kasamatsu, H.; Hawthorne, M. F. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 238.
28. Pan, X. Q.; Wang, H.; Shukla, S.; Sekido, M.; Adams, D. M.; Tjarks, W.; Barth, R. F.; Lee, R. J. Bioconjugate Chem. 2002, 13 (3), 435.
29. Chen, X.; Scgauder, S.; Potier, N.; Dorsselaer, A. V.; Pelczer, B. L.; Bassler, B. L.; Hughson, F. M. Nature, 2002, 415, 545.
30. O'Neill, M. A.; Eberhard, S.; Albersheim, P.; Darvill, A. G. Science 2001, 294, 846.
31. Höfte, H. Science 2001, 294, 795.
32. Uchimura, E.; Otsuka, H.; Okano, T.; Sakurai, Y.; Kataoka, K. Biotechnol. Bioeng. 2001, 72 (3), 307.
33. Zitte, C. A. Adv. Enzym. 1951, 12, 493.
34. Dunham, W. B.; MacNeal, W. J. J. Bacteriol. 1942, 44, 413.
35. Bryan, W. R.; Maver, M. E.; Moloney, J. B.; Thomas, M. A.; Sells, M. T. J. Natl. Cancer Inst. 1949. 10, 647.
36. Kerby, G. P.; Gowdy, R. A.; Dilon, E. S.; Dillon, M. L.; Csaky, T. Z.; Sharp, D. G.; Beard, J. W. J. Immunol. 1949, 63. 93.
37. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754.
38. Hood, D. W.; Makepeace, K.; Deadman, M. E.; Rest, R. F.; Thibault, P.; Martin, A.; Richards, J. C.; Moxon, E. R. Mol. Microbiol. 1999, 33 (4), 679.
39. Torgov, V. I.; Shashkov, A. S.; Jann, B.; Jann, K. Carbohydr. Res. 1995. 272 (1), 73.
40. Mattos-Guaraldi, A. L.; Cappelli, E. A.; Previato, J. O.; Formiga, L. C. D.; Andrade, A. F. B. FEMS Microbiol. Lett. 1999, 170, 159.
41. Roseman, S. Chem. Phys. Lipids 1970, 5, 270. Roth, S.; McGuire, E. J.; Roseman, S. J. Cell Biol. 1971, 57, 536.
42. Roseman, S. Chem. Phys. Lipids 1970, 5, 270. Roth, S.; McGuire, E. J.; Roseman, S. J. Cell Biol. 1971, 57, 536.
43. Glick, J. L.; Githens, S. Nature (London) 1965, 88, 208. Rahman, H.; Rosner, H.; Breer, H. J. Theor. Biol. 1976, 57, 231.
44. Glick, J. L.; Githens, S. Nature (London) 1965, 88, 208. Rahman, H.; Rosner, H.; Breer, H. J. Theor. Biol. 1976, 57, 231.
45. Schauer, R.; Schukla, A. K.; Schroder, C.; Muller, E. Pure Appl. Chem. 1984, 56, 907.
46. Morell, A. G.; Gregoriadis, G.; Scheinberg, I. H.; Hickman, J.; Ashwell, G. J. Biol. Chem. 1971, 246, 1461.
47. Chavin, S. I.; Weidner, M. J. Biol. Chem. 1984, 259, 3387.
48. Hirsch, R. L.; Griffin, D. E.; Winkelstein, J. A. J. Immunol. 1981, 127, 1740.
49. Wulff, G. Pure Appl. Chem. 1982, 54, 2093.
50. Akparov, V. H.; Stepanov, V. M. J. Chromatogr. 1978, 155, 329.
51. Gallop, P. M.; Paz, M. A.; Henson, E.; Latt, S. A. BioTechniques 1984, 2, 32.
52. Norrild, J. C. J. Chem. Soc., Perkin Trans. 2 2001, 719.
53. Bielecki, M.; Eggert, H.; Norrild, J. C. J. Chem. Soc., Perkin Trans. 2 1999, 449.
54. Fulton, S. Boronate Ligands in Biochemical Separations: Amicon: Danvers, Massachusetts, 1981.
55. Singhal, R. P.; DeSilva, S.; Shyamali, M. Adv. Chromatogr. 1992, 31, 293.
56. Barker, S. A.; Chopra, A. K.; Hatt, B. W.; Somers, P. J. Carbohydr. Res. 1973, 26, 33.
57. Sienkiewicz, P.; Roberts, D. J. Inorg. Nucl. Chem. 1980, 42, 1559.
58. Ferrier, R. J. Adv. Carbohydr. Chem. Biochem. 1978, 35, 31.
59. 0 denotes the total sugar.
60. Each spectrum was resolved into two components, and the peak areas were calculated with the Lorentzian function.
61. Sinton, S. W. Macromolecules 1987, 20, 2430.
62. Mori, Y.; Suzuki, A.; Yoshino, K.; Kakihana, H. Pigment Cell Res. 1989, 2, 273.
63. Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 1083.
64. Makkee, M.; Kieboom, A. P. G.; van Bekkum, H. Recl. Trav. Chim. Pays-Bas 1985, 104, 230.
65. Norrild, J. C.; Eggert, H. J. Am. Chem. Soc, 1995, 117, 1479.
66. Friebolin, H.; Kunzelmann, P.; Supp, M.; Brossmer, R.; Keilich, G.; Ziegler, D. Tetrahedron Lett. 1981, 22, 1383.
67. Ogura, H.; Furuhata, K.; Itoh, M.; Shitori, Y. Carbohydr. Res. 1986, 158, 37.
68. Hisamitsu, I. Ph.D. Thesis, Science University of Tokyo, Noda, Chiba, 1997.
69. Simple diols, such as ethylene glycol, assume a trans conformation in solution due to repulsion of the hydroxyls and, thus, have scarce interaction with borate. The strength of borate interaction with other polyols, as measured by titration, was in the order of glycerol < erythritol < adonitol < arabitol < mannitol.
70. Wiskur, S. L.; Lavigne, J. J.; Ait-Haddou, H.; Lynch, V.; Chiu, Y. H.; Canary, J. W.; Anslyn, E. V. Org. Lett. 2001, 3, 1311.
71. Hisamitsu, I.; Kataoka, K.; Okano, T.; Sakurai, Y. Pharm. Res. 1997, 14, 289.
72. Cai, S. X.; Keana, J. F. W. Bioconjugate Chem. 1991, 2, 317.
73. Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273.
74. van den Berg, R.; Peters, J. A.; van Bekkum, H. Carbohydr. Res. 1994, 253, 1.
75. Gorin, P. A. J.; Mazurek, M. Can. J. Chem. 1973, 51, 3277.
76. Norrild, J. C.; Eggert, H. J. Chem. Soc., Perkin Trans. 2 1996, 2583.
77. Shull, B. K.; Spielvogel, D. E.; Head, G.; Gopallaswamy, R.; Sankar, S.; Devito, K. J. Pharm. Sci. 2000, 89, 215.
78. Kibbis, R. N.; Osborne, S. E.; Glick, G. D.; Goldstein, I. J. J. Biol. Chem. 1993, 268 (25), 18524.
79. Miller, R. L.; Collawn, J. F., Jr.; Fish, W. W. J. Biol. Chem. 1982. 257, 7574.
80. Melton, L. D.; Morris, E. R.; Rees, D. A.; Thom, D. J. Chem. Soc., Perkin Trans. 2 1979, 2, 10.
81. Boeseken, J. Adv. Carbohydr. Chem. 1949, 4, 189.