Fluorescence-mediated sensing of guanosine derivatives based on multitopic hydrogen bonding

Abstract

The fluorescence emission of receptor 1 is selectively quenched upon binding of a guanosine derivative by five hydrogen bonds.

References

1. J. Rebek, Jr., Acc. Chem. Res., 1990, 23, 399; A. D. Hamilton, E. Fan, S. V. Arman, S. J. Geib and J. Yang, Philos. Trans. R. Soc. Lond. A, 1993, 345, 57.
2. M. Inouye, K. Kim and T. Kitao, J. Am. Chem. Soc., 1992, 114, 778.
3. M. Abe, J. Otsuki and K. Araki, Chem. Lett., 1993, 1541.
4. M. M. H. Khalil, F. C. De Schryver, H. Keller and J.-M. Lehn, Supramol. Sci., 1995, 2, 175–182.
5. O. S. Wolfbeis, Fiber Optic Chemical Sensors and Biosensors, CRC Press, Boca Raton, FL, 1991.
6. J. Pranata, S. G. Wierschke and W. L. Jorgensen, J. Am. Chem. Soc., 1991, 113, 2810.
7. T. W. Bell, Z. Hou, S. C. Zimmerman and P. A. Thiessen, Angew. Chem., Int. Ed. Engl., 1995, 34, 2163 For guanine receptors with three hydrogen bonding sites (see also ref. 2): A. D. Hamilton and N. Pant, J. Chem. Soc., Chem. Commun., 1988, 765; T. Ishida, H. Iyo, H. Ueda, M. Doi and M. Inoue, J. Chem. Soc., Chem. Commun., 1990, 217; H. Furuta, K. Kuruta and J. L. Sessler, J. Am. Chem. Soc., 1991, 113, 4706; T. K. Park, J. Schroeder and J. Rebek, Jr., Tetrahedron, 1991, 47, 2507; S. Metzger and B. Lippert, Angew. Chem., Int. Ed. Engl., 1996, 35, 1228; S. Amemiya, P. Bühlmann, K. Tohda and Y. Umezawa, Anal. Chim. Acta, in the press; K. Tohda, S. Amemiya, S. Nagahora, S. Tanaka, T. Ohki, P. Bühlmann and Y. Umezawa, unpublished results.
8. S. Nishizawa, P. Bühlmann, M. Iwao and Y. Umezawa, Tetrahedron Lett., 1995, 36, 6483; P. Bühlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron, 1997, 53, 1647.
9. W. E. Morf, K. Seiler, B. Lehmann, C. Behringer, K. Hartman and W. Simon, Pure Appl. Chem., 1989, 61, 1613.
10. K. Tohda, R. Naganawa, X. M. Lin, M. Tange, K. Umezawa, K. Odashima, Y. Umezawa, H. Furuta and J. L. Sessler, Sens. Actuators B, 1993, 13/14, 669.