Selective carbohydrate recognition by synthetic receptors in aqueous solution

Current Organic Chemistry

Volumn 7, Issue 1, 2003, Pages 81-102

  Striegler, Susanne ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CARBOHYDRATE; LIGAND; POLYMER; WATER;

AQUEOUS SOLUTION; BINDING ASSAY; CARBOHYDRATE ANALYSIS; CARBOHYDRATE TRANSPORT; CHEMICAL STRUCTURE; CHIRALITY; COVALENT BOND; ELECTROCHEMISTRY; ION EXCHANGE; LIQUID MEMBRANE; MEDICAL RESEARCH; MOLECULAR INTERACTION; MOLECULAR PROBE; MOLECULAR RECOGNITION; MOLECULAR STABILITY; MOLECULE; ONLINE MONITORING; REVIEW; SENSOR; SIGNAL DETECTION; STRUCTURE ANALYSIS;

EID: 0037253406     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033373201     Document Type: Review

References (123)

1. Mrksich, M. Chem. Soc. Rev., 2000, 29, 267.
2. Lis, H.; Sharon, N. Chem. Rev., 1998, 98, 637.
3. Seto, N.O.L.; Evans, S. Curr. Org. Chem., 2000, 4, 411.
4. Sacchettini, J.C.; Baum, L.G.; Brewer, C.F. Biochemistry, 2001, 40, 3009.
5. Hebert, E. Biosci. Rep., 2000, 20, 213.
6. Mengerink, K.J.; Vacquier, V.D. Glycobiology, 2001, 11, 37R.
7. Mouricout, M.; Vedrine, B. In Lectins Pathol., Caron, M.; Seve, A.-P., Eds.; Harwood Academic Publishers: Amsterdam, Neth., 2000; pp. 157-171.
8. Bhat, N.; Ward, H.D. In Lectins Pathol., Harwood Academic Publishers: Amsterdam, Neth., 2000; pp. 173-200.
9. Kerner, W. Exp. Clin. Endocrinol. Diabet., 2001, 109, S341.
10. Freckmann, G.; Kalatz, B.; Pfeiffer, B.; Hoss, U.; Haug, C. Exp. Clin. Endocrinol. Diabet., 2001, 109, S347.
11. McNichols, R.J.; Cote, G.L. J. Biomed. Opt., 2000, 5, 5.
12. James, T.D.; Shinkai, S. In Host-Guest Chemistry - Mimetic Approaches to Study Carbohydrate Recognition, Penadés, S., Ed.; Springer-Verlag: Berlin, Heidelberg, 2002; 218.
13. Hartley, J.H.; James, T.D.; Ward, C.J. J. Chem. Soc., Perkin Trans. 1, 2000, 3155.
14. Davis, A.P.; Wareham, R.S. Angew. Chem., Int. Ed. Engl., 1999, 38, 2979.
15. Inouye, M. J. Synth. Org. Chem. Jpn., 2000, 58, 1077.
16. James, T.D.; Sandanayake, K.R.A.S.; Shinkai, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1911.
17. DiCesare, N.; Lakowicz, J.R. J. Phys. Chem. A, 2001, 105, 6834.
18. Steinborn, D.; Junicke, H. Chem. Rev., 2000, 100, 4283.
19. Gyurcsik, B.; Nagy, L. Coord. Chem. Rev., 2000, 203, 81.
20. Shinkai, S.; Ikeda, M.; Sugasaki, A.; Takeuchi, M. Acc. Chem. Res., 2001, 34, 494.
21. London, R.E.; A., G.S. J. Am. Chem. Soc., 1994, 116, 2562.
22. Moore, A.N.J.; Wayner, D.D.M. Can. J. Chem.-Rev. Can. Chim., 1999, 77, 681.
23. Friedman, S.; Pace, B.; Pizer, R. J. Am. Chem. Soc., 1974, 96, 5381.
24. Pizer, R.; Babcock, L. Inorg. Chem., 1977, 16, 1677.
25. Babcock, L.; Pizer, R. Inorg. Chem., 1980, 19, 56.
26. London, R.E.; A., G.S. J. Am. Chem. Soc., 1994, 116, 2570.
27. Norrild, J.C.; Sotofte, I. J. Chem. Soc., Perkin Trans. 2, 2001, 727.
28. Nagai, Y.; Kobayashi, K.; Toi, H.; Aoyama, Y. Bull. Chem. Soc. Jpn., 1993, 66, 2965.
29. Oshima, K.; Toi, H.; Aoyama, Y. Carbohydr. Lett., 1995, 1, 223.
30. Eggert, H.; Frederiksen, J.; Morin, C.; Norrild, J. C. J. Org. Chem., 1999, 64, 3846.
31. Norrild, J. C.; Eggert, H. J. Am. Chem. Soc., 1995, 117, 1479.
32. Burgemeister, T.; Grobeeinsler, R.; Grotstollen, R.; Mannschreck, A.; Wulff, G. Chem. Ber., 1981, 114, 3403.
33. Wulff, G. Pure Appl. Chem., 1982, 54, 2093.
34. James, T.D.; Sandanayake, K.R.A.S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc., 1995, 117, 8982.
35. Ori, A.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1995, 1771.
36. Höpfl, H. J. Organomet. Chem., 1999, 581, 129.
37. Norrild, J.C. J. Chem. Soc., Perkin Trans. 2, 2001, 719.
38. Norrild, J.C.; Sotofte, I. J. Chem. Soc., Perkin Trans. 2, 2002, 303.
39. Lorand, J.P.; Edwards, J.O. J. Org. Chem., 1959, 24, 769.
40. Uggla, R.; Sundberg, M.R.; Nevalainen, V. Acta Chem. Scand., 1999; 53, 34.
41. Lakowicz, J.R. Principles of Fluorescence Spectroscopy, Plenum Press: New York, 1999.
42. James, T.D.; Sandanayake, K.R.A.S.; Shinkai, S. Nature, 1995, 374, 345.
43. DiCesare, N.; Lakowicz, J.R. Anal. Biochem., 2001, 294, 254.
44. Koumoto, K.; Takeuchi, M.; Shinkai, S. Supramol. Chem., 1998, 9, 203.
45. Kijima, H.; Takeuchi, M.; Robertson, A.; Shinkai, S.; Cooper, C.; James, T.D. J. Chem. Soc., Chem. Commun., 1999, 2011.
46. Berndt, K.W.; Gryczynski, I.; Lakowicz, J.R. Rev. Sci. Instrum., 1990, 61, 1816.
47. Szmacinski, H.; Lakowicz, J.R. Sens. Actuators B, 1995, 29, 16.
48. Burch, C.L.; Lakowicz, J.R. Biophys. J., 1995, 68, 1574.
49. Bambot, S.B.; Rao, G.; Romauld, M.; Carter, G.M.; Sipior, J.; Terpetschnig, E., Lakowicz, J.R. Biosens. Bioelectron., 1995, 10, 643.
50. Appleton, B.; Gibson, T.D. Sens. Actuator B, 2000, 65, 302.
51. Wang, W.; Gao, S.H.; Wang, B.H. Org. Lett., 1999, 1, 1209.
52. Gao, S.H.; Wang, W.; Wang, B.H. Bioorg. Chem., 2001, 29, 308.
53. Arimori, S.; Bell, M.L.; Oh, C.S.; Frimat, K.A.; James, T.D. J. Chem. Soc., Chem. Commun., 2001, 1836.
54. Lawrence, D.S.; Jiang, T.; Levett, M. Chem. Rev., 1995, 95, 2229.
55. Tong, A.J.; Yamauchi, A.; Hayashita, T.; Zhang, Z.Y.; Smith, B.D.; Teramae, N. Anal. Chem., 2001, 73, 1530.
56. Rehm, D.; Weller, A. Israel J. Chem., 1970, 8, 259.
57. DeSilva, A.P.; Gunaratne, H.Q.N.; Gunnlaugsson, T.; Huxley, J.M.; McCoy, C.P.; Rademacher, J.T.; Rice, T.E. Chem. Rev., 1997, 97, 1515.
58. Ward, C.J.; Patel, P.; Ashton, P.R.; James, T.D. J. Chem. Soc., Chem. Commun., 2000, 229.
59. Sandanayake, K.R.A.S.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1994, 1083.
60. Ward, C.J.; Patel, P.; James, T.D. J. Chem. Soc., Perkin Trans. 1, 2002, 462.
61. Ward, C.J.; Patel, P.; James, T.D. Org. Lett., 2002, 4, 447.
62. Roland, J.R.; McKusick, B.C. J. Am. Chem. Soc., 1961, 83, 1652.
63. McKusick, B.C.; Heckert, R.E.; Cairns, T.L.; Coffman, D.D.; Mower, H.F. J. Am. Chem. Soc., 1958, 80, 2806.
64. Arimori, S.; Bosch, L.I.; Ward, C.J.; James, T.D. Tetrahedron Lett., 2001, 42, 4553.
65. James, T.D.; Samankumara Sandanayake, K.R.A.; Shinkai, S. Angew. Chem. Int. Ed. Engl., 1996, 35, 1910.
66. James, T.D.; Linnane, P.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1996, 281.
67. DiCesare, N.; Lakowicz, J.R. Org. Lett., 2001, 3, 3891.
68. Davis, C.J.; Lewis, P.T.; McCarroll, M.E.; Read, M.W.; Cueto, R.; Strongin, R.M. Org. Lett., 1999, 1, 331.
69. Lewis, P.T.; Davis, C.J.; Cabell, L.A.; He, M.; Read, M.W.; McCarroll, M.E.; Strongin, R.M. Org. Lett., 2000, 2, 589.
70. Wiskur, S.L.; Ait-Haddou, H.; Lavigne, J.J.; Anslyn, E.V. Acc. Chem. Res., 2001, 34, 963.
71. Cabell, L.A.; Monahan, M.K.; Anslyn, E.V. Tetrahedron Lett., 1999, 40, 7753.
72. Lavigne, J.J.; Anslyn, E.V. Angew. Chem., Int. Ed. Engl., 1999, 38, 3666.
73. Springsteen, G.; Wang, B.H. J. Chem. Soc., Chem. Commun., 2001, 1608.
74. Arimori, S.; Ward, C.J.; James, T.D. Tetrahedron Lett., 2002, 43, 303.
75. Rusin, O.; Kral, V. Tetrahedron Lett., 2001, 42, 4235.
76. Camara, J.N.; Suri, C.R.; Cappuccio, F.E.; Wessling, R.A.; Singaram, B. Tetrahedron Lett., 2002, 43, 1139.
77. Takeuchi, M.; Yoda, S.; Imada, T.; Shinkai, S. Tetrahedron, 1997, 53, 8335.
78. Mizuno, T.; Takeuchi, M.; Shinkai, S. Tetrahedron, 1999, 55, 9455.
79. Mizuno, T.; Yamamoto, M.; Takeuchi, M.; Shinkai, S. Tetrahedron, 2000, 56, 6193.
80. Takeuchi, M.; Mizuno, T.; Shinkai, S.; Shirakami, S.; Itoh, T. Tetrahedron Asymmetry, 2000, 11, 3311.
81. Shiramkami, S.; Itoh, T. Tetrahedron Asymmetry, 2000, 11, 2823.
82. Richards, C.J.L., A. J. Tetrahedron Asymmetry, 1998, 9, 2377.
83. Togni, A. Angew. Chem., Int. Ed. Engl., 1996, 35, 1475.
84. Yam, V.W.W.; Kai, A.S.F. J. Chem. Soc., Chem. Commun., 1998, 109.
85. Mizuno, T.; Fukumatsu, T.; Takeuchi, M.; Shinkai, S. J. Chem. Soc.-Perkin Trans. 1, 2000, 407.
86. Bowden, K. Chem. Rev., 1996, 66, 119.
87. Yamamoto, H.; Ori, A.; Ueda, K.; Dusemund, C.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1996, 407.
88. Nicolas, M.; Fabre, B.; Simonet, J. Electrochim. Acta, 2001, 46, 1179.
89. Mizuno, T.; Takeuchi, M.; Hamachi, I.; Nakashima, K.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2, 2, 1998, 2281.
90. Brown, R.S.; Luong, J.H.T. Electroanalysis, 1994, 6, 391.
91. Di Luccio, M.; Smith, B.D.; Kida, T.; Borges, C.P.; Alves, T.L.M. J. Membr. Sci., 2000, 174, 217.
92. Bartsch, R.A.; Douglas, J.D. In Chemical Separations with Liquid Membranes, Bartsch, R.A.; Way, J.D., Eds.; American Chemical Society: Washington, D.C., 1996; ACS Symp. Ser. 642, pp. 1-10.
93. Kemperman, A.J.B.; Bargeman, D.; Van Den Boomgaard, T.; Strathmann, H. Sep. Sci. Technol., 1996, 31, 2733.
94. Smith, B.D. In Chemical Separations with Liquid Membranes, Bartsch, R.A.; Way, J.D., Eds.; American Chemical Society: Washington, D.C., 1996; ACS Symp. Ser. 642, pp. 194-205.
95. Gardiner, S.J.; Smith, B.D.; Duggan, P.J.; Karpa, M.J.; Griffin, G.J. Tetrahedron, 1999, 55, 2857.
96. Draffin, S.P.; Duggan, P.J.; Duggan, S.A.M. Org. Lett., 2001, 3, 917.
97. Karpa, M.J.; Duggan, P.J.; Griffin, G.J.; Freudigmann, S.J. Tetrahedron, 1997, 53, 3669.
98. Tsukagoshi, K.; Shinkai, S. J. Org. Chem., 1991, 56, 4089.
99. Tbeur, N.; Rhlalou, T.; Hlaibi, M.; Langevin, D.; Metayer, M.; Verchere, J.F. Carbohydr. Res., 2000, 329, 409.
100. Rhlalou, T.; Ferhat, M.; Frouji, M.A.; Langevin, D.; Me'tayer, M.; Verche're, J.-F. J. Membr. Sci., 2000, 168, 63.
101. Wulff, G. Chem. Rev., 2002, 102, 1.
102. Wulff, G.; Schauhoff, S. J. Org. Chem., 1991, 56, 395.
103. Wulff, G.; Haarer, J. Makrom. Chem., 1991, 192, 1329.
104. Wulff, G. In Frontiers in Biosensorics I - Fundamental Aspects, Scheller, F.W.; Schubert, F.; Fedrowitz, J., Eds.; Birkhäuser Verlag: Basel, 1997; pp. 13-26.
105. Haupt, K.; Mosbach, K. Chem. Rev., 2000, 100, 2495.
106. Sallacan, N.; Zayats, M.; Bourenko, T.; Kharitonov, A.B.; Willner, I. Anal. Chem., 2002, 74, 702.
107. Suri, C.R.; Mishra, G.C. Biosens. Bioelectron., 1996, 11, 1199.
108. Lahav, M.; Katz, E.; Doron, A.; Patolsky, F.; Willner, I. J. Am. Chem. Soc., 1999, 121, 862.
109. Panasyuk, T.L.; Mirsky, V.M.; Piletsky, S.A.; Wolfbeis, O.S. Anal. Chem., 1999, 71, 4609.
110. Mirsky, V.M.; Hirsch, T.; WO Patent 9928047; June 10, 1999 to Wolfbeis, Otto Samuel.
111. Malitesta, C.; Losito, I.; Zambonin, P.G. Anal. Chem., 1999, 71, 1366.
112. Cheng, Z.L.; Wang, E.K.; Yang, X.R. Biosens. Bioelectron., 2001, 16, 179.
113. Chen, G.H.; Guan, Z.B.; Chen, C.T.; Fu, L.T.; Sundaresan, V.; Arnold, F.H. Nat. Biotechnol., 1997, 15, 354.
114. Arnold, F.H.; Guan, Z.; Chen, C.-T.; Chen, G.; US Patent 6063637; May 16, 2000 to California Institute of Technology.
115. Chen, G.; Sundaresan, V.; Arnold, F.H. Polym. Prepr. [Am. Chem. Soc., Div. Polym. Chem.], 1997, 38, 378.
116. Arnold, F.H.; Zheng, W.G.; Michaels, A.S. J. Membr. Sci., 2000, 167, 227.
117. Striegler, S. Tetrahedron, 2001, 57, 2349.
118. Arnold, F.H.; Striegler, S.; Sundaresan, V. In Molecular and Ionic Recognition with Imprinted Polymers, Bartsch, R.A.; Maeda, M., Eds.; American Chemical Society: Washington, D.C., 1998; ACS Symp. Ser. 703, pp. 109-118.
119. Plunkett, S.D.; Arnold, F.H. J. Chromatogr. A, 1995, 708, 19.
120. Janda, K.D.; Weinhouse, M.I.; Schloeder, D.M.; Lerner, R.A.; Benkovic, S.J. J. Am. Chem. Soc., 1990, 112, 1274.
121. Strigler, S.; Tewes, E. Eur. J. Inorg. Chem., 2002, 2, 487.
122. Kobayashi, H.; Nakashima, K.; Ohshima, E.; Hisaeda, Y.; Hamachi, I.; Shinkai, S. J. Chem. Soc., Perkin Trans. 2, 2000, 5, 997.
123. Gabai, R.; Sallacan, N.; Chegel, V.; Bourenko, T.; Katz, E.; Willner, I. J. Phys. Chem. B, 2001, 105, 8196.