A New Bile Acid-based Ditopic Adenine/Biotin Receptor with Convergent Carboxyl Groups

References

• Jeffrey , G. A. and Saenger , W. 1991 . Hydrogen Bonding in Biological Structures , Berlin : Springer Verlag .
   Google Scholar
• Hamilton , A. D. , Pant , N. and Muchldorf , A. 1988 . Pure Appl. Chem. , 60 : 533 (b) Meissner, R. S. and Rebek, J. Jr. and de Mendoza, J., Science, 270, 1495 (1995). (c) Yoon, S. S. and Still, W. C., J. Am. Chem. Soc., 115, 823 (1993). (d) Bell, D. A. and Anslyn, E. V., Tetrahedron, 51, 7161 (1995).
   Web of Science ®Google Scholar
• Saenger , W. 1984 . Principles of Nucleic Acid Structures , New York : Springer-Verlag .
   Google Scholar
• Thuong , N. T. and Hélène , C. 1993 . Angew. Chem. Int. Ed. Engl. , 32 : 666
   Web of Science ®Google Scholar
• Thunnisen , A.-M. , Dijkstra , W. H. A. J. , Kalk , K. H. , Rozeboom , H. J. , Engel , H. , Keck , W. and Dijkstra , B. W. 1994 . Nature , 367 : 750 For an example of protein-DNA interaction see, For a recent review see Klug, A. and Choo, Y., Curr. Opn. Str. Biol., 7, 117 (1997).
   Google Scholar
• Hamilton , A. D. 1991 . Bioorg. Chem. Frontiers , 2 : 115 For a general overview of synthetic receptors for nucleobases see
   Google Scholar
• Kyogoku , Y. , Lord , R. C. and Rich , A. 1966 . Science , 154 : 5109 (b) Katz, L., J. Mol. Biol., 44, 279 (1969). (c) Nowick, J. S., Cao, T. and Noronha, G., J. Am. Chem. Soc., 115, 3548 (1994). (d) Sartorius, J. and Schneider, H.-J., Chem. Eur. J., 2, 1446 (1996).
   Google Scholar
• Goswami , S. and Hamilton , D. A. 1989 . J. Am. Chem. Soc. , 111 : 3425 (b) Rebek, J. Jr., (1990) Acc. Chem. Res., 23, 399. (c) Conn, M. M., Deslongchamp, G., De Mendoza, J. and Rebek, J. Jr., J. Am. Chem. Soc., 115, 3548 (1993).
   Web of Science ®Google Scholar
• Zimmerman , S. C. and Wu , W. 1989 . J. Am. Chem. Soc. , 111 : 8056
   Google Scholar
• Leppkins , R. and Vögtle , F. 1981 . Angew. Chem. Int. Ed. Engl. , 20 : 396 (b) Adrian, J. C. and Wilcox, C. S., J. Am. Chem. Soc., 111, 8055 (1989). For an adenine binding polymer see (c) Spivak, D., Gilmore, M. A. and Shea, K. J., J. Am. Chem. Soc., 119, 4388 (1997).
   Google Scholar
• Davis , A. P. 1993 . Chem. Soc. Rev. , 22 : 243 (b) Bonar-Law, R. P. and Sanders, J. K. M., J. Am. Chem. Soc., 117, 259 (1995). (c) Hsieh, H.-P., Muller, J. G. and Burrows, C. S., J. Am. Chem. Soc., 116, 12077 (1994). (d) Cheng, Y. A., Suenaga, T. and Still, W. C., (1996). J. Am. Chem. Soc., 118, 1813, (e) Janout, V., Lanier, M. and Regen, S. L., J. Am. Chem. Soc., 118, 1573 (1996). (f) Venkatesan, P., Cheng, Y. and Kahne, D., J. Am. Chem. Soc., 116, 6955 (1994). (g) Davis, A. P., Perry, J. J. and Williams, R. P., J. Am. Chem. Soc., 119, 1793 (1997).
   Web of Science ®Google Scholar
• De'Souza , L. J. and Maitra , U. 1996 . J. Org. Chem. , 61 : 9494 (b) Maitra, U., Rao, P., Vijayakumar, P., Balasubramanian, S. and Mathew, L., Tetrahedron Lett., 39, 3255 (1998).
   Google Scholar
• Nowick , J. S. , Chen , J. S. and Noronha , G. 1993 . J. Am. Chem. Soc. , 115 : 7636 9-N-butyladenine was used for this purpose and was prepared according to a literature procedure. See
   Web of Science ®Google Scholar
• PCMODEL for Windows, version 5.13. The input conformations were kept as close to the binding geometry as possible.
   Google Scholar
• Oppenauer , R. V. 1966 . Monatsch. , 97 : 62
   Google Scholar
• Selected Spectroscopic Data on 4: FABMS 726 (M+ + Na+ + H+); 1H-NMR (DMSO-d6, 400 MHz) 0.76 (d, 3H), 0.79 (s, 3H), 0.94 (s, 3H), 1.00–2.20 (m, 26H), 3.51 (s, 3H), 4.83 (s, 1H), 5.31 (s, 1H), 7.58 (t, 1H), 7.88 (d, 1H), 8.09–8.14 (5H), 8.39 (s, 1H), 13.15 (br.s, 2H); 13C-NMR (DMSO-d6, 75 MHz) 12.16, 17.24, 22.51, 23.00, 25.49, 25.77, 26.04, 30.18, 31.66, 33.41, 34.05, 35.05, 40.89, 44.91, 47.40, 49.61, 51.07, 74.29, 76.38, 129.126, 129.694, 130.36, 131.12, 132.24, 132.58, 133.63, 135.19, 164.23, 164.39, 166.34, 166.48, 173.52; IR, cm−1, nujol: 1700, 3200–3700 [α]D 24 = +66(c, = 1.4, THF) Found C, 70.00; H, 7.36. Reqd. C41H50O10C, 70.06; H, 7.10.
   Google Scholar
• The solubility of 4, in CHCl3 is only 1.64 mM at 27°C. However, we were able to solubilise as much as 6 mM of host 4, in the presence of the guest.
   Google Scholar
• The acid was initially dissolved in THF, required volumes added into the NMR tubes and evaporated to dryness in vacuo for 3 h.
   Google Scholar
• Lancelot , G. 1977 . J. Am. Chem. Soc. , 88 : 7037 It is well documented in all these examples that these aromatic signals can be followed to obtain the association constant (Ka ) with reliability.
   Google Scholar