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DOI: 10.1039/A804352C (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1999, 363-368

Zn2+ inclusion complexes of endodentate tripodands as carbonic anhydrase-inspired artificial esterases. Part 2.1 Micellar systems

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Rick Jairam, Pierre G. Potvin and Steven Balsky

Abstract

Facile syntheses of two lipophilic, endo-tridentate tris-imidazole podands (3 and 4) are reported. These were designed for micellar media, where pre-organization for metal binding was anticipated to better reproduce the active site of carbonic anhydrase (CA). pH-Metric titrations and p-nitrophenyl acetate (pNPOAc) hydrolyses were carried out in the presence of Zn2+ and the results compared with those obtained with hydrophilic tripodand varieties. The results confirm stronger metal binding with the micelle-bound ligands and show reasonably low pKa values near 8 for the deprotonation of metal-bound H2O, as well as evidence for a proton shuttling analogous to that seen in the enzyme. The second-order rate constant for pNPOAc hydrolysis by [Zn(3)OH]+ was estimated at 0.19(1) M–1 s–1, the second-highest value measured for a biomimetic CA model.

References

  1. Part 1. R. Jairam and P. G. Potvin, J. Org. Chem., 1992, 57, 4136 Search PubMed.
  2. S. Lindskog, in Zinc Enzymes, ed. T. G. Spiro, Wiley-Interscience, New York, 1983, p. 77 Search PubMed; K. K. Kannan, M. Ramanadham and T. A. Jones, in Biology and Chemistry of the Carbonic Anhydrases, ed. R. E. Tashian and D. Hewett-Emmett, Annals of the New York Academy of Sciences, vol. 429, New York Academy of Sciences, New York, 1984, 49 Search PubMed.
  3. D. N. Silverman and S. Lindskog, Acc. Chem. Res., 1988, 21, 30 CrossRef CAS.
  4. E. A. Eriksson, T. A. Jones and A. Liljas, in Zinc Enzymes, ed. I. Bertini, C. Luchinat, W. Maret and M. Zeppezauer, Birkhäuser, Boston, 1986, p. 317 Search PubMed; A. Vedani, D. W. Huhta and S. P. Jacober, J. Am. Chem. Soc., 1989, 111, 4075 Search PubMed; K. M. Merz Jr., R. Hoffmann and M. S. Dewar, J. Am. Chem. Soc., 1989, 111, 5636 CrossRef CAS.
  5. Tris (imidazolyl) alkanes and -alkanols: R. S. Brown and J. Huguet, Can. J. Chem., 1980, 58, 889 Search PubMed; C. C. Tang, D. Davalian, P. Huang and R. Breslow, J. Am. Chem. Soc., 1978, 100, 3918 CAS; R. Breslow, J. T. Hunt, R. Smiley and T. Tarnowski, J. Am. Chem. Soc., 1983, 105, 5337 CrossRef CAS Tris (pyridyl) phosphine and -arsine: R. Gregorzik, J. Wirbser and H. Vahrenkamp, Chem. Ber., 1992, 125, 1575 CrossRef CAS Tris (benz- imidazolylmethyl) amines: R. Gregorzik, U. Hartmann and H. Vahrenkamp, Chem. Ber., 1994, 127, 2117 Search PubMed; U. Hartmann, R. Gregorzik and H. Vahrenkamp, Chem. Ber., 1994, 127, 2123 CAS Tris (pyrazolyl) methanes: C. Titze, J. Hermann and H. Vahrenkamp, Chem. Ber., 1995, 128, 1095 Search PubMed 1,1,1-Tris (methylaminomethyl) ethane: W. Brandt, J. Wirbser, A. K. Powell and H. Vahrenkamp, Z. Naturforsch., Teil B, 1991, 46, 440 CrossRef CAS Tris (pyridylmethyl) amine: N. N. Murthy and K. D. Karlin, J. Chem. Soc., Chem. Commun., 1993, 1236 CAS Cyclohexane-1,3,5-triamine derivatives: B. Greener, M. H. Moore and P. H. Walton, J. Chem. Soc., Chem. Commun., 1996, 27 Search PubMed; U. Brand and H. Vahrenkamp, Inorg. Chim. Acta, 1992, 198, 663 CrossRef CAS Bis (pyridylmethyl) amine and bis (benzimidazolylmethyl) amine: J. Wirbser and H. Vahrenkamp, Z. Naturforsch., Teil B, 1992, 47, 962 Search PubMed 2,6-Diacetylpyridine-derived Schiff bases: D. A. Edwards, M. F. Mahon, W. R. Martin, K. C. Molloy, P. E. Fanwick and R. A. Walton, J. Chem. Soc., Dalton Trans., 1990, 3161 CAS.
  6. Tris (imidazolyl) phosphines: (a) J. Huguet and R. S. Brown, J. Am. Chem. Soc., 1980, 102, 7572 CrossRef; (b) R. S. Brown, N. J. Curtis and J. Huguet, J. Am. Chem. Soc., 1981, 103, 6953 CrossRef CAS; (c) R. S. Brown, D. Salmon, N. J. Curtis and S. Kusuma, J. Am. Chem. Soc., 1982, 104, 3188 CrossRef CAS; (d) H. Slebocka-Tilk, J. L. Cocho, Z. Frakman and R. S. Brown, J. Am. Chem. Soc., 1984, 106, 2421 CrossRef CAS; (e) R. S. Brown, M. Zamkanei and J. L. Cocho, J. Am. Chem. Soc., 1984, 106, 5222 CrossRef CAS.
  7. Tris (pyrazolyl) hydroborates: (a) A. Looney, R. Han, K. McNeill and G. Parkin, J. Am. Chem. Soc., 1993, 115, 4690 CrossRef CAS; (b) R. Alsfasser, M. Ruf, S. TroWmenko and H. Vahrenkamp, Chem. Ber., 1993, 126, 703 CAS; (c) M. Ruf, K. Weis and H. Vahrenkamp, J. Chem. Soc., Chem. Commun., 1994, 135 RSC; (d) R. Alsfasser, A. K. Powell, S. TroWmenko and H. Vahrenkamp, Chem. Ber., 1993, 126, 685 CAS.
  8. Macrocyclic polyamines: (a) P. Wooley, Nature, 1975, 258, 677 CAS; (b) S. Gellman, R. Petter and R. Breslow, J. Am. Chem. Soc., 1986, 108, 2388 CrossRef CAS; (c) R. Breslow and S. Singh, Bioorg. Chem., 1988, 16, 408 CrossRef CAS; (d) E. I. Kimura, T. Shiota, T. Koike, M. Shiro and M. Kodama, J. Am. Chem. Soc., 1990, 112, 5805 CrossRef CAS; (e) E. Kimura, Prog. Inorg. Chem., 1994, 41, 443 CAS.
  9. 2,2′-Biimidazole: C. Kirchner and B. Krebs, Inorg. Chem., 1987, 26, 3569 Search PubMed 3,5-Di (pyridyl) triazoles: U. Hartmann and H. Vahrenkamp, Inorg. Chim. Acta, 1995, 239, 13 CrossRef CAS.
  10. C. Wendelstorf, S. Warzeska, E. Kövári and R. Krämer, J. Chem. Soc., Dalton Trans., 1996, 3087 RSC.
  11. M. H. Wong, M.Sc. Thesis, York University, 1988; R. Jairam, M.Sc. Thesis, York University, 1991.
  12. Y. Moroi, Micelles: Theoretical and Applied Aspects, Plenum Press, New York, 1992, p. 41 Search PubMed.
  13. Phenanthrolinylamine, phenanthrolinylmethyl- and pyridylmethyl-histamines: J. G. J. Weijnen, A. Koudjis and J. F. J. Engbersen, J. Chem. Soc., Perkin Trans. 2, 1991, 1121 Search PubMed Mono- and diimid-azolylmethanols: K. Ogino, K. Inoue and W. Tagaki, Tetrahedron Lett., 1992, 4191 RSC; T. Fujita, K. Ogino and W. Tagaki, Chem. Lett., 1988, 981 Search PubMed; K. Ogino, N. Kashihara, T. Fujita, T. Ueda, T. Isaka and W. Tagaki, Chem. Lett., 1987, 1303 CrossRef CAS Pyridylmethanols: R. Fornasier, P. Scrimin, P. Tecilla and U. Tonellato, J. Am. Chem. Soc., 1989, 111, 224 CAS; R. Fornasier, D. Milani, P. Scrimin and U. Tonellato, J. Chem. Soc., Perkin Trans. 2, 1986, 233 CAS; G. De Santi, P. Scrimin and U. Tonellato, Tetrahedron Lett., 1990, 31, 4791 Search PubMed.
  14. E. Kimura, H. Hashimoto and T. Koike, J. Am. Chem. Soc., 1996, 118, 10963 CrossRef CAS.
  15. P. G. Potvin, R. Gau, C. M. Unrau and N. K. Gehl, Can. J. Chem., 1989, 67, 1363 CAS.
  16. T. Kunitake, N. Kimizuka, N. Higashi and N. Nakashima, J. Am. Chem. Soc., 1984, 106, 1978 CrossRef CAS.
  17. K. Ogino, K. Nishi, H. Yamamoto, T. Yoshida and W. Tagaki, Tetrahedron Lett., 1990, 7023 CrossRef CAS.
  18. N. Al-Awadi and A. Williams, J. Org. Chem, 1990, 55, 2001 CrossRef CAS; J. H. Fendler and E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, 1975, p. 104 Search PubMed.
  19. C. A. Salata, M.-T. Youinou and C. J. Burrows, Inorg. Chem., 1991, 30, 3454 CrossRef CAS.
  20. R. Breslow and L. Overman, J. Am. Chem. Soc., 1970, 92, 1075 CrossRef CAS.
  21. B. Zhang and R. Breslow, J. Am. Chem. Soc., 1997, 119, 1676 CrossRef CAS.
  22. J. J. HarrowWeld, V. Norris and A. M. Sargeson, J. Am. Chem. Soc., 1976, 98, 7282 CrossRef CAS.
  23. J. Chin, M. Banaszczyk, V. Jubian and X. Zou, J. Am. Chem. Soc., 1989, 111, 186 CrossRef CAS.
  24. P. G. Potvin, Can. J. Chem., 1990, 68, 2198 CAS.
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