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Saccharide-Selective Boronic Acid Based Photoinduced Electron Transfer (PET) Fluorescent Sensors

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Creative Chemical Sensor Systems

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 277))

Abstract

The ability to monitor the presence of analytes within physiological, environmental and industrial systems is of crucial importance. However, due to the scale at which recognition events occur on the molecular level, gathering this information poses a non-trivial challenge. Therefore, robust chemical molecular sensors with the capacity to detect chosen molecules selectively and to signal this presence have attracted considerable attention over recent years.

Of particular interest is the real-time monitoring of saccharides in aqueous systems, such as d-glucose in blood. To this end the covalent pair-wise interaction between boronic acids and saccharides has been exploited.

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References

  1. Desiraju GR (2001) Nature 412:397

    Article  PubMed  ADS  CAS  Google Scholar 

  2. Malmström BG (1997) Nobel lectures in chemistry (1991–1995). World Scientific, Singapore

    Google Scholar 

  3. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Chem Rev 97:1515

    Article  PubMed  Google Scholar 

  4. Czarnik AW (1993) Fluorescent chemosensors for ion and molecule recognition. American Chemical Society Books, Washington DC

    Book  Google Scholar 

  5. Jelinek R, Kolusheva S (2004) Chem Rev 104:5987

    Article  PubMed  CAS  Google Scholar 

  6. James TD, Linnane P, Shinkai S (1996) Chem Commun, p 281

    Google Scholar 

  7. James TD, Sandanayake KRAS, Shinkai S (1996) Angew Chem, Int Ed Engl 35:1911

    Article  CAS  Google Scholar 

  8. Phillips MD, James TD (2004) J Fluoresc 14:549

    Article  PubMed  CAS  Google Scholar 

  9. James TD, Shinkai S (2002) Top Curr Chem 218:159

    Article  CAS  Google Scholar 

  10. Davis AP, James TD (2005) In: Schrader T, Hamilton AD (eds) Functional synthetic receptors. Wiley, Weinheim, p 45

    Chapter  Google Scholar 

  11. James TD (2005) In: Hall DG (ed) Boronic acids in organic synthesis and chemical biology. Wiley, Weinheim, p 441

    Google Scholar 

  12. Striegler S (2003) Curr Org Chem 7:81

    Article  CAS  Google Scholar 

  13. Wang W, Gao X, Wang B (2002) Curr Org Chem 6:1285

    Article  CAS  Google Scholar 

  14. Cao H, Heagy MD (2004) J Fluoresc 14:569

    Article  PubMed  CAS  Google Scholar 

  15. Fang H, Kaur G, Wang B (2004) J Fluoresc 14:481

    Article  PubMed  CAS  Google Scholar 

  16. Granda-Valdes M, Badia R, Pina-Luis G, Diaz-Garcia ME (2000) Quim Anal 19:38

    CAS  Google Scholar 

  17. Moschou EA, Sharma BV, Deo SK, Daunert S (2004) J Fluoresc 14:535

    Article  PubMed  CAS  Google Scholar 

  18. Shinkai S, Takeuchi M (2004) Biosens Bioelectron 20:1250

    Article  PubMed  CAS  Google Scholar 

  19. Shinkai S, Takeuchi M (2005) Bull Chem Soc Jpn 78:40

    Article  CAS  Google Scholar 

  20. Davis AP, Wareham RS (1999) Angew Chem Int Ed 38:2978

    Article  Google Scholar 

  21. Klein E, Crump MP, Davis AP (2004) Angew Chem Int Ed 44:298

    Article  Google Scholar 

  22. Böeseken J (1949) Adv Carbohydr Chem 4:189

    Google Scholar 

  23. Böeseken J (1913) Chemische Berichte 46:2612

    Google Scholar 

  24. Kuivila HG, Keough AH, Soboczenski EJ (1954) J Org Chem 19:780

    Article  CAS  Google Scholar 

  25. Wolfrom MI, Solms J (1956) J Org Chem 21:815

    Article  CAS  Google Scholar 

  26. Lappert MF (1956) Chem Rev 56:959

    Article  CAS  Google Scholar 

  27. Torssel K (1957) Ark Kemi 10:473

    Google Scholar 

  28. Lorand JP, Edwards JO (1959) J Org Chem 24:769

    Article  CAS  Google Scholar 

  29. Hartley JH, Phillips MD, James TD (2002) New J Chem 26:1228

    Article  CAS  Google Scholar 

  30. Soundararajan S, Badawi M, Kohlrust CM, Hageman JH (1989) Anal Biochem 178:125

    Article  PubMed  CAS  Google Scholar 

  31. Springsteen G, Wang B (2002) Tetrahedron 58:5291

    Article  CAS  Google Scholar 

  32. Yuchi A, Tatebe A, Kani S, James TD (2001) Bull Chem Soc Jpn 74:509

    Article  CAS  Google Scholar 

  33. Juillard J, Gueguen N (1967) Comp Rend Acad Sci C 264:259

    CAS  Google Scholar 

  34. Friedman S, Pace B, Pizer R (1974) J Am Chem Soc 96:5381

    Article  CAS  Google Scholar 

  35. Edwards JO, Sederstrom RJ (1961) J Phys Chem 65:862

    Article  CAS  Google Scholar 

  36. Bosch LI, Fyles TM, James TD (2004) Tetrahedron 60:11175

    Article  CAS  Google Scholar 

  37. Martell AE, Smith RM (1976) Critical stability constants. Plenum, New York

    Google Scholar 

  38. DiCesare N, Lakowicz JR (2001) Anal Biochem 294:154

    Article  PubMed  CAS  Google Scholar 

  39. Friedman S, Pizer R (1975) J Am Chem Soc 97:6059

    Article  CAS  Google Scholar 

  40. Pizer R, Selzer R (1983) Inorg Chem 23:3023

    Article  Google Scholar 

  41. Kustin K, Pizer R (1969) J Am Chem Soc 91:317

    Article  CAS  Google Scholar 

  42. Babcock L, Pizer R (1980) Inorg Chem 19:56

    Article  CAS  Google Scholar 

  43. Pizer R, Tihal C (1992) Inorg Chem 31:3243

    Article  CAS  Google Scholar 

  44. Ferrier RJ (1978) Adv Carbohydr Chem Biochem 35:31

    Article  CAS  Google Scholar 

  45. Shinkai S, Tsukagoshi K, Ishikawa Y, Kunitake T (1991) J Chem Soc, Chem Commun, p 1039

    Google Scholar 

  46. Finch A, Gardner PJ, McNamara PM, Wellum GR (1970) J Chem Soc A, p 3339

    Google Scholar 

  47. Tsukagoshi K, Shinkai S (1991) J Org Chem, p 4089

    Google Scholar 

  48. Kondo K, Shiomi Y, Saisho M, Harada T, Shinkai S (1992) Tetrahedron, p 8239

    Google Scholar 

  49. Bissell RA, Desilva AP, Gunaratne HQN, Lynch PLM, Maguire GEM, Sandanayake KRAS (1992) Chem Soc Rev 21:187

    Article  CAS  Google Scholar 

  50. Böhmer M, Enderlein J (2003) Chem Phys Chem 4:793

    PubMed  Google Scholar 

  51. Moerner WE, Fromm DP (2003) Rev Sci Instrum 74:3597

    Article  ADS  CAS  Google Scholar 

  52. Ambrose WP, Goodwin PM, Jett JH, Van Orden A, Werner JH, Keller RA (1999) Chem Rev 99:2929

    Article  PubMed  CAS  Google Scholar 

  53. Sauer M (2003) Angew Chem Int Ed 42:1790

    Article  CAS  Google Scholar 

  54. Epstein JR, Walt DR (2003) Chem Soc Rev 32:203

    Article  PubMed  CAS  Google Scholar 

  55. Fehr M, Lalonde S, Ehrhardt DW, Frommer WB (2004) J Fluoresc 14:603

    Article  PubMed  CAS  Google Scholar 

  56. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Nieuwenhuizen M (1996) Chem Commun, p 1967

    Google Scholar 

  57. He HR, Mortellaro MA, Leiner MJP, Young ST, Fraatz RJ, Tusa JK (2003) Anal Chem 75:549

    Article  PubMed  CAS  Google Scholar 

  58. Tudos AJ, Besselink GAJ, Schasfoort RBM (2001) Lab Chip 1:83

    Article  PubMed  CAS  Google Scholar 

  59. Schlebusch H, Paffenholz I, Zerback R, Leinberger R (2001) Clin Chim Acta 307:107

    Article  PubMed  CAS  Google Scholar 

  60. Badugu R, Lakowicz JR, Geddes CD (2004) Bioorg Med Chem 13:113

    Article  CAS  Google Scholar 

  61. Yoon J, Czarnik AW (1992) J Am Chem Soc 114:5874

    Article  CAS  Google Scholar 

  62. James TD, Sandanayake KRAS, Shinkai S (1994) Angew Chem, Int Ed Engl 33:2207

    Article  Google Scholar 

  63. James TD, Sandanayake KRAS, Shinkai S (1995) Nature 374:345

    Article  ADS  CAS  Google Scholar 

  64. Wulff G (1982) Pure Appl Chem 54:2093

    Article  Google Scholar 

  65. James TD, Sandanayake K, Shinkai S (1994) J Chem Soc, Chem Commun, p 477

    Google Scholar 

  66. James TD, Sandanayake KRAS, Iguchi R, Shinkai S (1995) J Am Chem Soc 117:8982

    Article  CAS  Google Scholar 

  67. Höpfl H (1999) J Organomet Chem 581:129

    Article  Google Scholar 

  68. Wiskur SL, Lavigne JJ, Ait-Haddou H, Lynch V, Hung Chiu Y, Canary JW, Anslyn EV (2001) Org Lett 3:1311

    Article  PubMed  CAS  Google Scholar 

  69. Franzen S, Ni W, Wang B (2003) J Phys Chem B 107:12942

    Article  CAS  Google Scholar 

  70. Ni WJ, Kaur G, Springsteen G, Wang BH, Franzen S (2004) Bioorg Chem 32:571

    Article  PubMed  CAS  Google Scholar 

  71. Zhao J, Davidson MG, Mahon MF, Kociok-Köhn G, James TD (2004) J Am Chem Soc 126:16179

    Article  PubMed  CAS  Google Scholar 

  72. Bhat KL, Braz V, Laverty E, Bock CW (2004) THEOCHEM J Mol Struct 712:9

    Article  CAS  Google Scholar 

  73. Bhat KL, Howard NJ, Rostami H, Lai JH, Bock CW (2005) THEOCHEM J Mol Struct 723:147

    Article  CAS  Google Scholar 

  74. Morrison JD, Letsinger RL (1964) J Org Chem 29:3405

    Article  CAS  Google Scholar 

  75. Zhu L, Shabbir SH, Gray M, Lynch VM, Sorey S, Anslyn EV (2006) J Am Chem Soc 128:1222

    Article  PubMed  CAS  Google Scholar 

  76. Bielecki M, Eggert H, Norrild JC (1999) J Chem Soc, Perkin Trans 2, p 449

    Google Scholar 

  77. Norrild JC, Eggert H (1995) J Am Chem Soc 117:1479

    Article  CAS  Google Scholar 

  78. Nicholls MP, Paul PKC (2004) Org Biomol Chem 2:1434

    Article  PubMed  CAS  Google Scholar 

  79. Angyal SJ (1991) Adv Carbohydr Chem Biochem 49:19

    Article  Google Scholar 

  80. Angyal SJ (1984) Adv Carbohydr Chem Biochem 42:15

    Article  CAS  Google Scholar 

  81. Norrild JC, Eggert H (1996) J Chem Soc, Perkin Trans 2, p 2583

    Google Scholar 

  82. Eggert H, Frederiksen J, Morin C, Norrild JC (1999) J Org Chem 64:3846

    Article  CAS  Google Scholar 

  83. Cooper CR, James TD (1998) Chem Lett, p 883

    Google Scholar 

  84. Nagai Y, Kobayashi K, Toi H, Aoyama Y (1993) Bull Chem Soc Jpn 66:2965

    Article  CAS  Google Scholar 

  85. Yang W, He H, Drueckhammer DG (2001) Angew Chem Int Ed 40:1714

    Article  CAS  Google Scholar 

  86. Sandanayake KRAS, James TD, Shinkai S (1995) Chem Lett, p 503

    Google Scholar 

  87. Appleton B, Gibson TD (2000) Sens Actuators B 65:302

    Article  Google Scholar 

  88. Cooper CR, James TD (2000) J Chem Soc, Perkin Trans 1, p 963

    Google Scholar 

  89. Phillips MD (2000) Fluorescent phosphate sensors. M NatSc (Chem) Dissertation, The University of Birmingham, UK

    Google Scholar 

  90. Arimori S, Bell ML, Oh CS, Frimat KA, James TD (2001) Chem Commun, p 1836

    Google Scholar 

  91. Arimori S, Bell ML, Oh CS, Frimat KA, James TD (2002) J Chem Soc, Perkin Trans 1, p 803

    Google Scholar 

  92. Perrin DD, Dempsey B (1974) Buffers for pH and metal ion control. Chapman Hall, London

    Google Scholar 

  93. Lakowicz JR (1999) Principles of fluorescence spectroscopy. Plenum, New York

    Google Scholar 

  94. Arimori S, Bell ML, Oh CS, James TD (2002) Org Lett 4:4249

    Article  PubMed  CAS  Google Scholar 

  95. Jin T (1999) Chem Commun, p 2491

    Google Scholar 

  96. Arimori S, Consiglio GA, Phillips MD, James TD (2003) Tetrahedron Lett 44:4789

    Article  CAS  Google Scholar 

  97. Barboiu M, Supuran CT, Scozzafava A, Briganti F, Luca C, Popescu G, Cot L, Hovnanian N (1997) Liebigs Ann Chem, p 1853

    Google Scholar 

  98. Galema SA, Blandamer MJ, Engberts J (1990) J Am Chem Soc 112:9665

    Article  CAS  Google Scholar 

  99. Fabri D, Williams MAK, Halstead TK (2005) Carbohydr Res 340:889

    Article  PubMed  CAS  Google Scholar 

  100. Galema SA, Blandamer MJ, Engberts J (1992) J Org Chem 57:1995

    Article  CAS  Google Scholar 

  101. Janado M, Yano Y (1985) Bull Chem Soc Jpn 58:1913

    Article  CAS  Google Scholar 

  102. Yano Y, Tanaka K, Doi Y, Janado M (1988) Bull Chem Soc Jpn 61:2963

    Article  CAS  Google Scholar 

  103. Fischer E (1894) Ber Dtsch Chem Ges 27:2985

    Article  CAS  Google Scholar 

  104. Lemieux RU, Spohr U (1994) Adv Carbohydr Chem Biochem 50:1

    Article  PubMed  CAS  Google Scholar 

  105. Warner DT (1962) Nature 196:1055

    Article  ADS  CAS  Google Scholar 

  106. Walkinshaw MD (1987) J Chem Soc, Perkin Trans 2, p 1903

    Google Scholar 

  107. Lemieux RU (1996) Acc Chem Res 29:373

    Article  CAS  Google Scholar 

  108. Westmark PR, Smith BD (1994) J Am Chem Soc 116:9343

    Article  CAS  Google Scholar 

  109. Draffin SP, Duggan PJ, Duggan SAM (2001) Org Lett 3:917

    Article  PubMed  CAS  Google Scholar 

  110. Gardiner SJ, Smith BD, Duggan PJ, Karpa MJ, Griffin GJ (1999) Tetrahedron 55:2857

    Article  CAS  Google Scholar 

  111. Westmark PR, Gardiner SJ, Smith BD (1996) J Am Chem Soc 118:11093

    Article  CAS  Google Scholar 

  112. Riggs JA, Litchfield RK, Smith BD (1996) J Org Chem 61:1148

    Article  CAS  Google Scholar 

  113. Morin GT, Hughes MP, Paugam MF, Smith BD (1994) J Am Chem Soc 116:8895

    Article  CAS  Google Scholar 

  114. Yang W, Gao S, Gao X, Karnati VVR, Ni W, Wang B, Hooks WB, Carson J, Weston B (2002) Bioorg Med Chem Lett 12:2175

    Article  PubMed  CAS  Google Scholar 

  115. Karnati VV, Gao X, Gao S, Yang W, Ni W, Sankar S, Wang B (2002) Bioorg Med Chem Lett 12:3373

    Article  PubMed  CAS  Google Scholar 

  116. Yang W, Fan H, Gao X, Gao S, Karnati VVR, Ni W, Hooks WB, Carson J, Weston B, Wang B (2004) Chem Biol 11:439

    Article  PubMed  CAS  Google Scholar 

  117. Stones D, Manku S, Lu XS, Hall DG (2004) Chem Eur J 10:92

    Article  CAS  Google Scholar 

  118. Carey FA, Sundberg RJ (2000) Advanced organic chemistry. Kluwer Academic/Plenum, New York

    Google Scholar 

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  1. Department of Chemistry, University of Bath, BA2 7AY, Bath, UK

    Tony D. James

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Thomas Schrader

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James, T.D. (2007). Saccharide-Selective Boronic Acid Based Photoinduced Electron Transfer (PET) Fluorescent Sensors. In: Schrader, T. (eds) Creative Chemical Sensor Systems. Topics in Current Chemistry, vol 277. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_110

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