Urea porphyrins as simple receptors for sugars

Chemical Communications

Volumn 18, Issue , 2002, Pages 2108-2109

  Ladomenou, Kalliopi ^a   Bonar Law, Richard P ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOHYDRATE BINDING PROTEIN; CARBOHYDRATE DERIVATIVE; PORPHYRIN; RECEPTOR; SUGAR; UREA;

AMINO ACID SUBSTITUTION; ARTICLE; PROTEIN BINDING;

EID: 0036402660     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b206646g     Document Type: Article

References (30)

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6. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
7. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
8. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
9. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
10. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
11. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
12. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
13. Some recent examples (a) M. Mazik and W. Sickling, Chem. Eur. J., 2001, 7, 664; (b) S. Tamaru, M. Yamamoto, S. Shinkai, A. B. Khasanov and T. W. Bell, Chem. Eur. J., 2001, 7, 5270; (c) J. Bitta and S. Kubik, Org. Lett., 2001, 3, 2637; (d) H.-J. Kim, Y.-H. Kim and J.-I. Hong, Tetrahedron Lett., 2001, 42, 5049; (e) J. M. Benito, M. Gomez-Garcia, J. L. Jimenez Blanco, C. Ortiz Mellet and J. M. Garcia Fernandez, J. Org. Chem., 2001, 66, 1366; (f) M. Mazik, H. Bandmann and W. Sickling, Angew. Chem., Int. Ed., 2000, 39, 551; (g) N. Sugimoto, D. Miyoshi and J. Zou, Chem. Commun., 2000, 2295; (h) D. K. Smith, A. Zingg and F. Diederich, Helv. Chim. Acta., 1999, 82, 1225; (i) M. Inouye, K. Takahashi and H. Nakazumi, J. Am. Chem. Soc., 1999, 121, 341.
14. Kral et al. have reported binding of sugars by porphyrins in polar solvents: O. Rusin, K. Lang and V. Kral, Chem. Eur. J., 2002, 8, 655.
15. Recent porphyrin-based receptors (a) H.-J. Schneider, L. Tianjun, M. Sirish and V. Malinovski, Tetrahedron, 2002, 58, 779; (b) C. Z. Wang, Z. A. Zhu, Y. Li, Y. T. Chen, X. Wen, F. M. Miao, W. L. Chan and A. S. C. Chan, New J. Chem., 2001, 25, 801; (c) T. Mitzutani, K. Wada and S. Kitagawa, J. Org. Chem., 2000, 65, 6097; (d) M. Inamo and I. Yoneda, Inorg. Chem. Commun., 1999, 331; (e) H. Imai, H. Munakata, A. Takahashi, S. Nakagawa, Y. Ihara and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1999, 2565.
16. Recent porphyrin-based receptors (a) H.-J. Schneider, L. Tianjun, M. Sirish and V. Malinovski, Tetrahedron, 2002, 58, 779; (b) C. Z. Wang, Z. A. Zhu, Y. Li, Y. T. Chen, X. Wen, F. M. Miao, W. L. Chan and A. S. C. Chan, New J. Chem., 2001, 25, 801; (c) T. Mitzutani, K. Wada and S. Kitagawa, J. Org. Chem., 2000, 65, 6097; (d) M. Inamo and I. Yoneda, Inorg. Chem. Commun., 1999, 331; (e) H. Imai, H. Munakata, A. Takahashi, S. Nakagawa, Y. Ihara and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1999, 2565.
17. Recent porphyrin-based receptors (a) H.-J. Schneider, L. Tianjun, M. Sirish and V. Malinovski, Tetrahedron, 2002, 58, 779; (b) C. Z. Wang, Z. A. Zhu, Y. Li, Y. T. Chen, X. Wen, F. M. Miao, W. L. Chan and A. S. C. Chan, New J. Chem., 2001, 25, 801; (c) T. Mitzutani, K. Wada and S. Kitagawa, J. Org. Chem., 2000, 65, 6097; (d) M. Inamo and I. Yoneda, Inorg. Chem. Commun., 1999, 331; (e) H. Imai, H. Munakata, A. Takahashi, S. Nakagawa, Y. Ihara and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1999, 2565.
18. Recent porphyrin-based receptors (a) H.-J. Schneider, L. Tianjun, M. Sirish and V. Malinovski, Tetrahedron, 2002, 58, 779; (b) C. Z. Wang, Z. A. Zhu, Y. Li, Y. T. Chen, X. Wen, F. M. Miao, W. L. Chan and A. S. C. Chan, New J. Chem., 2001, 25, 801; (c) T. Mitzutani, K. Wada and S. Kitagawa, J. Org. Chem., 2000, 65, 6097; (d) M. Inamo and I. Yoneda, Inorg. Chem. Commun., 1999, 331; (e) H. Imai, H. Munakata, A. Takahashi, S. Nakagawa, Y. Ihara and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1999, 2565.
19. Recent porphyrin-based receptors (a) H.-J. Schneider, L. Tianjun, M. Sirish and V. Malinovski, Tetrahedron, 2002, 58, 779; (b) C. Z. Wang, Z. A. Zhu, Y. Li, Y. T. Chen, X. Wen, F. M. Miao, W. L. Chan and A. S. C. Chan, New J. Chem., 2001, 25, 801; (c) T. Mitzutani, K. Wada and S. Kitagawa, J. Org. Chem., 2000, 65, 6097; (d) M. Inamo and I. Yoneda, Inorg. Chem. Commun., 1999, 331; (e) H. Imai, H. Munakata, A. Takahashi, S. Nakagawa, Y. Ihara and Y. Uemori, J. Chem. Soc., Perkin Trans. 2, 1999, 2565.
20. For acyclic triamide receptors see refs. 3(a) and 3(f).
21. C. Lee, D. H. Lee and J.-I. Hong, Tetrahedron Lett., 2001, 42, 8665;
22. R. C. Jagessar, M. Shang, W. R. Scheidt and D. H. Burns, J. Am. Chem. Soc., 1998, 120, 11684.
23. J. P. Collman, Z. Wang and A. Straumanis, J. Org. Chem., 1998, 63, 2424.
24. Treated as a sequential association, K values for 1:2 complexes were two to three orders of magnitude lower than for the first binding. Titrations were more or less isosbestic since 1:1 and 1:2 species have similar spectra.
25. R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 1995, 117, 259.
26. Measured K values for this porphyrin were unusually variable, possibly because Zn2c binds water quite strongly.
27. Recent studies of porphyrin aggregation in polar solvents (a) P. Kubat, K. Lang, P. Anzenbacher Jr., K. Jursikova, V. Kral and B. Ehrenberg, J. Chem. Soc., Perkin Trans. 2, 2000, 933; (b) K. Kano, K. Fukuda, H. Wakami, R. Nishiyabu and R. F. Pasternack, J. Am. Chem. Soc., 2000, 122, 7494.
28. Recent studies of porphyrin aggregation in polar solvents (a) P. Kubat, K. Lang, P. Anzenbacher Jr., K. Jursikova, V. Kral and B. Ehrenberg, J. Chem. Soc., Perkin Trans. 2, 2000, 933; (b) K. Kano, K. Fukuda, H. Wakami, R. Nishiyabu and R. F. Pasternack, J. Am. Chem. Soc., 2000, 122, 7494.
29. 3 were measured for Zn2a and 2b, treating aggregation as a simple monomer-dimer equilibrium.
30. NH ∼ 0.35, 34% receptor saturation. Methyl β-glucoside or the α anomer 4 did not produce downfield shifts of the NH protons under the same conditions.