Molecular Design of Highly Selective and Sensitive "Sugar Tweezers" from Boronic Acid-Appended μ-Oxo-bis[porphinatoiron(III)]s

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 5, 1998, Pages 1117-1123

  Takeuchi, Masayuki ^a   Imada, Tomoyuki ^a   Shinkai, Seyi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001416893     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1117     Document Type: Article

References (57)

1. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
2. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
3. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
4. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
5. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
6. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
7. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
8. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
9. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
10. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
11. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
12. General hydrogen-bonding systems, see: J. Rebek, Jr., Angew. Chem., 102, 261 (1990); Angew. Chem., Int. Ed. Engl., 29, 245 (1990); A. D. Hamilton and D. van Engen, J. Am. Chem. Soc., 109, 5035 (1987); S. Goswami and A. D. Hamilton, J. Am. Chem. Soc., 111, 3425 (1989); T. R. Kelly and P. M. Maguire, J. Am. Chem. Soc., 109, 6549 (1987); T. R. Kelly, C. Zhao, and G. J. Bridger, J. Am. Chem. Soc., 111, 3744 (1989); M. C. Etter and T. W. Paunto, J. Am. Chem. Soc., 110, 5896 (1988); M. C. Etter and D. A. Adsmond, J. Chem. Soc., Chem. Commun., 1990, 589; V. Hedge, P. Madhukar, J. D. Madura, and R. P. Thummel, J. Am. Chem. Soc., 112, 4549 (1990); T. W. Bell and L. Liu, J. Am. Chem. Soc., 110, 3673 (1988); H. Furuta and J. L. Sessler, J. Am. Chem. Soc., 113, 4706 (1991); A. Galan, D. Andreu, A. M. Echavarren, P. Prados, and J. de Mendoza, J. Am. Chem. Soc., 114, 1511 (1992).
13. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
14. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
15. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
16. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
17. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
18. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
19. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
20. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
21. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
22. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
23. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
24. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
25. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
26. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
27. Hydrogen-bonding systems for saccharides and related compounds, see: Y. Aoyama, Y. Tanaka, and S. Sugahara, J. Am. Chem. Soc., 111, 5397 (1989); Y. Tanaka, Y. Ubukata, and Y. Aoyama, Chem. Lett., 1989, 1905; Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, and Y. Aoyama, J. Am. Chem. Soc., 114, 10302 (1992); K. Kobayashi, Y. Asakawa, Y. Kato, and Y. Aoyama, J. Am. Chem. Soc., 114, 10307 (1992); R. P. Bonar-Law, A. P. Davis, and B. A. Murray, Angew. Chem., 102, 1497 (1990); Angew. Chem., Int. Ed. Engl., 29, 1407 (1990); N. Greenspoon and E. Wachtel, J. Am. Chem. Soc., 113, 7233 (1991); K. Kano, K. Yoshiyasu, and S. Hashimoto, J. Chem. Soc., Chem. Commun., 1988, 801; C.-Y. Huang, L. A. Cabell, V. Lynch, and E. V. Anslyn, J. Am. Chem. Soc., 114, 1900 (1992); C.-Y. Huang, L. A. Cabell, and E. V. Anslyn, J. Am. Chem. Soc., 116, 2778 (1994); A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 116, 6081 (1994); P. B. Savage and S. H. Gellman, J. Am. Chem. Soc., 115, 10448 (1993); G. Das and A. D. Hamiltom, J. Am. Chem. Soc., 116, 11139 (1994); J. M. Coteron, C. Vicent, C. Bosso, and S. Penades, J. Am. Chem. Soc., 115, 10066 (1993); Y. Kikuchi, K. Kobayashi, and Y. Aoyama, J. Am. Chem. Soc., 114, 1351 (1992).
28. Hydrogen-bonding systems for the chiral recognition of saccharides, see: R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 117, 259 (1995); K. M. Bhattarai, R. P. Bonar-Low, A. P. Davis, and B. A. Murray, J. Chem. Soc., Chem. Commun., 1992, 752; R. Liu and W. C. Still, Tetrahedron Lett, 34, 2573 (1993); J. Cuntze, L. Owens, V. Aleazar, P. Seiler, and F. Diederich, Helv. Chim. Acta, 78, 367 (1995).
29. Hydrogen-bonding systems for the chiral recognition of saccharides, see: R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 117, 259 (1995); K. M. Bhattarai, R. P. Bonar-Low, A. P. Davis, and B. A. Murray, J. Chem. Soc., Chem. Commun., 1992, 752; R. Liu and W. C. Still, Tetrahedron Lett, 34, 2573 (1993); J. Cuntze, L. Owens, V. Aleazar, P. Seiler, and F. Diederich, Helv. Chim. Acta, 78, 367 (1995).
30. Hydrogen-bonding systems for the chiral recognition of saccharides, see: R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 117, 259 (1995); K. M. Bhattarai, R. P. Bonar-Low, A. P. Davis, and B. A. Murray, J. Chem. Soc., Chem. Commun., 1992, 752; R. Liu and W. C. Still, Tetrahedron Lett, 34, 2573 (1993); J. Cuntze, L. Owens, V. Aleazar, P. Seiler, and F. Diederich, Helv. Chim. Acta, 78, 367 (1995).
31. Hydrogen-bonding systems for the chiral recognition of saccharides, see: R. P. Bonar-Law and J. K. M. Sanders, J. Am. Chem. Soc., 117, 259 (1995); K. M. Bhattarai, R. P. Bonar-Low, A. P. Davis, and B. A. Murray, J. Chem. Soc., Chem. Commun., 1992, 752; R. Liu and W. C. Still, Tetrahedron Lett, 34, 2573 (1993); J. Cuntze, L. Owens, V. Aleazar, P. Seiler, and F. Diederich, Helv. Chim. Acta, 78, 367 (1995).
32. For comprehensive reviews for boronic acid-based saccharide receptors, see: T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Supramol. Chem., 6, 141 (1995); T. D. James, P. Linnane, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1996, 281.
33. For comprehensive reviews for boronic acid-based saccharide receptors, see: T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Supramol. Chem., 6, 141 (1995); T. D. James, P. Linnane, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1996, 281.
34. J. Yoon and A. W. Czarnik, J. Am. Chem. Soc., 114, 5874 (1995); L. K. Mohler and A. W. Czarnik, J. Am. Chem. Soc., 115, 2998 (1993).
35. J. Yoon and A. W. Czarnik, J. Am. Chem. Soc., 114, 5874 (1995); L. K. Mohler and A. W. Czarnik, J. Am. Chem. Soc., 115, 2998 (1993).
36. P. R. Westmark and B. D. Smith, J. Am. Chem. Soc., 116, 9343 (1994), and references cited therein.
37. Y. Nagai, K. Kobayashi, H. Toi, and Y. Aoyama, Bull. Chem. Soc. Jpn., 66, 2965 (1993).
38. G. Wulff, S. Krieger, B. Kubneweg, and A. Steigel, J. Am. Chem. Soc., 116, 409 (1994), and references cited therein.
39. For boronic acid-appended porphyrins, see: H. Toi, Y. Nagai, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043; T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557; T. Imada, H. Kijima, M. Takeuchi, and S. Shinkai, Tetrahedron, 52, 2817 (1996); H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975; S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
40. For boronic acid-appended porphyrins, see: H. Toi, Y. Nagai, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043; T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557; T. Imada, H. Kijima, M. Takeuchi, and S. Shinkai, Tetrahedron, 52, 2817 (1996); H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975; S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
41. For boronic acid-appended porphyrins, see: H. Toi, Y. Nagai, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043; T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557; T. Imada, H. Kijima, M. Takeuchi, and S. Shinkai, Tetrahedron, 52, 2817 (1996); H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975; S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
42. For boronic acid-appended porphyrins, see: H. Toi, Y. Nagai, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043; T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557; T. Imada, H. Kijima, M. Takeuchi, and S. Shinkai, Tetrahedron, 52, 2817 (1996); H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975; S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
43. For boronic acid-appended porphyrins, see: H. Toi, Y. Nagai, H. Kawabe, K. Aizawa, and H. Ogoshi, Chem. Lett., 1993, 1043; T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557; T. Imada, H. Kijima, M. Takeuchi, and S. Shinkai, Tetrahedron, 52, 2817 (1996); H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975; S. Arimori, M. Takeuchi, and S. Shinkai, J. Am. Chem. Soc., 118, 245 (1996).
44. The saccharide recognition by a metalloporphyrin using the hydrogen-bonding interaction was also reported: T. Mizutani, T. Murakami, N. Matsumi, T. Kurahashi, and H. Ogoshi, J. Chem. Soc., Chem. Commun., 1995, 1257.
45. S. Arimori, M. Takeuchi, and S. Shinkai, Chem. Lett, 1996, 77.
46. J. W. Buchler, in "The Porphyrins," ed by D. Dolphin, Academic Press, New York (1979), Vol. 1, Chap. 10, and references cited therein.
47. B. Cheng, J. D. Hobbs, P. G. Debrunner, J. Erlebacher, J. A. Shelnutt, and W. R. Scheldt, Inorg. Chem., 34, 102 (1995).
48. Preliminary communication: M. Takeuchi, T. Imada, and S. Shinkai, J. Am. Chem. Soc., 118, 10658 (1996).
49. C. Ercolani, M. Gardini, K. S. Murray, G. Pennesi, and G. Rossi, Inorg. Chem., 25, 3972 (1986); D. M. Kurtz, Jr., Chem. Rev., 90, 585 (1990).
50. C. Ercolani, M. Gardini, K. S. Murray, G. Pennesi, and G. Rossi, Inorg. Chem., 25, 3972 (1986); D. M. Kurtz, Jr., Chem. Rev., 90, 585 (1990).
51. Monosaccharides tested herein are glucose, galactose, mannose, arabinose, fructose, xylose, D-glucose-6-phosphate, and methyl α-D-glucoside.
52. Disaccharides tested herein are maltose, cellobiose, isomaltose, lactose, sucrose, gentiobiose, melibiose, palatinose, trehalose, and turanose.
53. A. Job, Annal. Chim., (10th series), 9, 113 (1928).
54. J. C. Norrild and H. Eggert, J. Am. Chem. Soc., 117, 1479 (1995); T. D. James, K. R. A. S. Sandanayake, R. Iguchi, and S. Shinkai, J. Am. Chem. Soc., 117, 8982 (1995); In the glucofuranoside form is immobilized whereas in the glucopyranoside form is immobilized.
55. J. C. Norrild and H. Eggert, J. Am. Chem. Soc., 117, 1479 (1995); T. D. James, K. R. A. S. Sandanayake, R. Iguchi, and S. Shinkai, J. Am. Chem. Soc., 117, 8982 (1995); In the glucofuranoside form is immobilized whereas in the glucopyranoside form is immobilized.
56. -1.
57. -1.