Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Anion Recognition of Cholic Acid-based Tripodal Receptor: A Chloride Selective Anion Receptor

  • Kim, Ki-Soo (Department of Applied Chemistry, Kyungpook National University) ;
  • Cho, Nam-Ju (Department of Applied Chemistry, Kyungpook National University) ;
  • Kim, Hong-Seok (Department of Applied Chemistry, Kyungpook National University)
  • Published : 2006.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Synthesis of cholic acid-based tripodal receptor (1) and its high chloride ion affinity in comparison with that of chenodeoxycholic acid (2) and lithocholic acid-based receptor (3) was achieved. Anion binding affinities of the receptors were evaluated $by\;^1H$ NMR and ITC titrations. Tripodal receptor 1 showed a selective affinity for $CI ^-$ over $Br ^-$, $I^-$, $H_2 PO _4\;^-$, and $CH _3 CO_2\;^-$. The selectivity of 1 for $CI ^-$ is about 3 times that of $Br ^-$, and 17 times that for $H_2 PO_4\;^-$.

Keywords

References

  1. Bianch, A.; Bowman-James, K.; Garcia-Espana, E., Supra-molecular Chemistry of Anions; Wiley-VCH: New York, 1997
  2. Schmidtchen, F. P.; Berger, M. Chem. Rev.1997, 97, 1609 https://doi.org/10.1021/cr9603845
  3. Bühlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593 https://doi.org/10.1021/cr970113+
  4. Antonisse, M. M. G.; Reinhoudt, D. N. Electroanalysis 1999,11, 1035 https://doi.org/10.1002/(SICI)1521-4109(199910)11:14<1035::AID-ELAN1035>3.0.CO;2-I
  5. Beer, P. D.; Gale, P. A. Angew. Chem. Int. Ed. 2001,40, 487
  6. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191 https://doi.org/10.1016/S0010-8545(02)00258-8
  7. Kirk, K. L. Biochemistry of the Halogens and Inorganic Halides;Plenum Press: New York, 1991
  8. Broughman, J. R.; Shank, L. P.; Takeguchi, W.; Schultz, B. D.;Iwamoto, T.; Mitchell, K. E.; Tomich, J. M. Biochemistry 2002, 41, 7350 and references therein https://doi.org/10.1021/bi016053q
  9. Capitán-Vallvey, L. F.; Guerrero, E. A.; Merelo, C. B.; Ramos,M. D. F. Anal. Bioanal. Chem. 2004, 380, 563 https://doi.org/10.1007/s00216-004-2735-6
  10. Bratov, A.;Abramova, N.; Domínguez, C. Anal. Chim. Acta 2004, 514, 99 https://doi.org/10.1016/j.aca.2004.01.034
  11. Xu, C.; Qin, Y.; Bakker, E. Talanta 2004, 63, 180 https://doi.org/10.1016/j.talanta.2003.10.033
  12. Yang,D.; Qu, J.; Li, W.; Zhang, Y.-H.; Ren, Y.; Wang, D.-P.; Wu, Y.-D.J. Am. Chem. Soc. 2002, 124, 12410 https://doi.org/10.1021/ja027073y
  13. Matile, S.; Som, A.; Sorde, N. Tetrahedron 2004, 60, 6405 https://doi.org/10.1016/j.tet.2004.05.052
  14. McNally, B. A.; Koulov, A. V.; Smith, B. D.; Joos, J.-B.; Davis, A.P. Chem. Commun. 2005, 1087
  15. Koulov, A. V.; Lambert, T. N.;Shukla, R.; Jain, M.; Boon, J. M.; Smith, B. D.; Li, H.; Sheppard,D. N.; Joos, J.-B.; Clare, J. P.; Davis, A. P. Angew. Chem. Int. Ed. 2003, 42, 4931 https://doi.org/10.1002/anie.200351957
  16. Schlesinger, P. H.; Ferdani, R.; Pajewski, R.;Pajewski, J.; Gokel, G. W. Chem. Commun. 2002, 840
  17. Davis, A. P.; Joos, J.-B. Coord. Chem. Rev.2003, 240, 143 https://doi.org/10.1016/S0010-8545(03)00020-1
  18. Urata, K.; Takaishi, N. Eur. J. Lipid Sci.Technol. 2001, 103, 29 https://doi.org/10.1002/1438-9312(200101)103:1<29::AID-EJLT29>3.0.CO;2-Q
  19. Wallimann, P.; Marti, T.; Furer, A.;Diederich, F. Chem. Rev.1997, 97, 1567 https://doi.org/10.1021/cr960373b
  20. Davis, A. P.; Gilmer,J. F.; Perry, J. J. Angew. Chem. Int. Ed. Engl. 1996, 35, 1312 https://doi.org/10.1002/anie.199613121
  21. Davis, A. P. Chem. Soc. Rev.1993, 22, 243 https://doi.org/10.1039/cs9932200243
  22. Maulucci, N.; De Riccardis, F.; Botta, C. B.; Casapullo, A.;Cressina, E.; Fregonese, M.; Tecilla, P.; Izzo, I. Chem. Commun. 2005, 1354
  23. Kolehmainen, E.; Koivukorpi, J.; Sievanen, E.;Kral, V. Supramol. Chem. 2005, 17, 437 https://doi.org/10.1080/10610270500127048
  24. Davis, A. P.; Perry, J. J.; Williams, R. P. J. Am. Chem. Soc. 1997, 119, 1793 https://doi.org/10.1021/ja9629930
  25. Ayling, A. J.; Perez-Payan, M. N.; Davis, A. P. J. Am. Chem. Soc. 2001, 123, 12716 https://doi.org/10.1021/ja016796z
  26. Ayling, A. J.; Broderick, S.; Clare, J.P.; Davis, A. P.; Perez-Payan, M. N.; Lahtinen, M.; Nissinen, M.J.; Rissanen, K. Chem Eur. J. 2002, 8, 2197 https://doi.org/10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J
  27. Sisson, A. L.;Clare, J. P.; Taylor, L. K.; Charmant, J. P. H.; Davis, A. P. Chem.Commun.2003, 2246
  28. Shim, J. H.; Jeong, I. S.; Lee, M. H.;Hong, H. P.; On, J. H.; Kim, K. S.; Kim, H.-S.; Kim, B. H.; Cha,G. S.; Nam, H. Talanta 2004, 63, 61 https://doi.org/10.1016/j.talanta.2003.12.050
  29. Clare, J. P.; Ayling, A. J.;Joos, J.-B.; Sisson, A. L.; Magro, G.; Perez-Payan, M. N.;Lambert, T. N.; Shukla, R.; Smith, B. D.; Davis, A. P. J. Am.Chem. Soc. 2005, 127, 10739 https://doi.org/10.1021/ja0524144
  30. Kim, K. S.; Kim, H.-S. Bull. Korean Chem. Soc.2004, 25,1411 https://doi.org/10.5012/bkcs.2004.25.9.1411
  31. Kim, K. S.; Kim, H.-S. Tetrahedron 2005, 61, 12366 https://doi.org/10.1016/j.tet.2005.09.082
  32. Boiochi,M.; Boca, L. D.; Gómez, E. D.; Fabbrizzi, L.; Licchelli, M.;Monzani, E. J. Am. Chem. Soc.2004, 126, 16507 https://doi.org/10.1021/ja045936c
  33. Cho, E. J.;Ryu, B. J.; Lee, Y. J.; Nam, K. C. Org. Lett. 2005, 7, 2607, andreferences therein https://doi.org/10.1021/ol0507470
  34. Fielding, L. Tetrahedron 2000, 56, 6151 https://doi.org/10.1016/S0040-4020(00)00492-0
  35. Job, P. Compt. Rend.1925, 180, 928
  36. Blanda, M. T.;Horner, J. H.; Newcomb, M. J. Org. Chem.1989, 54, 4626 https://doi.org/10.1021/jo00280a033
  37. Hynes, M. J. J. Chem. Soc. Dalton Trans.1993, 311
  38. Connors, K. A. Binding Constants; Wiley: New York, 1987
  39. MP2 calculation at the AM1 mode level was performed SPARTAN'04 for Windows (Wavefunction, Inc.: Irvine, CA)
  40. Kim, H.-S.; Choi, B.-S.; Kwon, K.-C.; Lee, S.-O.; Kwak, H. J.;Lee, C. H. Bioorg. Med. Chem. 2000, 8, 2059 https://doi.org/10.1016/S0968-0896(00)00128-0
  41. Savage, P. B.; Allman, G. W.; Willardson, B. M.; Driscoll, C. D.;Budge, L. P.; Li, C. J. Am. Chem. Soc. 1999, 121, 931 https://doi.org/10.1021/ja982938m

Cited by

  1. A New Acridine-Imidazolium-Based Cholestane Receptor for Anion Sensing vol.32, pp.spc8, 2011, https://doi.org/10.5012/bkcs.2011.32.8.2933
  2. Synthesis and Anion Binding Affinities of Novel Molecular Tweezers Based on Chenodeoxycholic Acid Bearing Different Lengths of Arm vol.27, pp.9, 2006, https://doi.org/10.5012/bkcs.2006.27.9.1445
  3. Steroid-based anion receptors and transporters vol.39, pp.10, 2006, https://doi.org/10.1039/b926225n