A tricyclic polyamide receptor for carbohydrates in organic media

Angewandte Chemie - International Edition

Volumn 37, Issue 16, 1998, Pages 2270-2273

  Davis, Anthony P ^a   Wareham, Richard S ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

Carbohydrates; Hydrogen bonds; Molecular recognition; Receptors; Supramolecular chemistry

Indexed keywords

EID: 0031709773     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980904)37:16<2270::AID-ANIE2270>3.0.CO;2-6     Document Type: Article

References (45)

1. For leading references to the biological significance of carbohydrate recognition, see: a) S. D. Rosen, C. R. Bertozzi, Curr. Opin. Cell Biol. 1994, 6, 663; b) N. Sharon, H. Lis, Essays Biochem. 1995, 30, 59; c) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321; d) W. I. Weis, K. Drickhamer, Annu. Rev. Biochem. 1996, 65, 441; e) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
2. For leading references to the biological significance of carbohydrate recognition, see: a) S. D. Rosen, C. R. Bertozzi, Curr. Opin. Cell Biol. 1994, 6, 663; b) N. Sharon, H. Lis, Essays Biochem. 1995, 30, 59; c) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321; d) W. I. Weis, K. Drickhamer, Annu. Rev. Biochem. 1996, 65, 441; e) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
3. For leading references to the biological significance of carbohydrate recognition, see: a) S. D. Rosen, C. R. Bertozzi, Curr. Opin. Cell Biol. 1994, 6, 663; b) N. Sharon, H. Lis, Essays Biochem. 1995, 30, 59; c) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321; d) W. I. Weis, K. Drickhamer, Annu. Rev. Biochem. 1996, 65, 441; e) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
4. For leading references to the biological significance of carbohydrate recognition, see: a) S. D. Rosen, C. R. Bertozzi, Curr. Opin. Cell Biol. 1994, 6, 663; b) N. Sharon, H. Lis, Essays Biochem. 1995, 30, 59; c) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321; d) W. I. Weis, K. Drickhamer, Annu. Rev. Biochem. 1996, 65, 441; e) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
5. For leading references to the biological significance of carbohydrate recognition, see: a) S. D. Rosen, C. R. Bertozzi, Curr. Opin. Cell Biol. 1994, 6, 663; b) N. Sharon, H. Lis, Essays Biochem. 1995, 30, 59; c) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321; d) W. I. Weis, K. Drickhamer, Annu. Rev. Biochem. 1996, 65, 441; e) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373.
6. The alkanol hydroxyl group, characteristic of carbohydrates, is of course capable of hydrogen-bond donation and acceptance, and can also ligate to metal ions. However, it is considerably less basic or acidic than many other groups involved in biochemical recognition, and forms correspondingly weaker interactions. See for example; D.H. Williams. Aldrichimica Acta 1991, 24, 71.
7. a) T. D. James, P. Linnane, S. Shinkai, Chem. Commun. 1996, 281;
8. b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038; Angew. Chem. Int. Ed. Engl. 1996, 35, 1911;
9. b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038; Angew. Chem. Int. Ed. Engl. 1996, 35, 1911;
10. c) B. D. Smith, Supramol. Chem. 1996, 7, 55.
11. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
12. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
13. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
14. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
15. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
16. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
17. Studies in aqueous media have either registered very low binding constants, or have employed carbohydrate substrates with hydrophobic appendages. For examples, see: Y. Aoyama, Y. Nagai, J. Otsuki, K. Kobayashi, H. Toi, Angew. Chem. 1992, 104, 785; Angew. Chem. Int. Ed. Engl. 1992, 31, 745; A. V. Eliseev, H.-J. Schneider, J. Am. Chem. Soc. 1994, 116, 6081; K. Kobayashi, Y. Asakawa, Y. Kato, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10307; B.-L. Poh, C. M. Tan, Tetrahedron 1993, 49, 9581; J. Jimenez-Barbero, E. Junquera, M. Martinpastor, S. Sharma, C. Vicent, S. Penades, J. Am. Chem. Soc. 1995, 117, 11 198; S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283.
18. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
19. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
20. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
21. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
22. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
23. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
24. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
25. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
26. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
27. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
28. Reports from this laboratory: a) R. P. Bonar-Law, A. P. Davis, B. A. Murray, Angew. Chem. 1990, 102, 1497; Angew. Chem. Int. Ed. Engl. 1990, 29, 1407; b) K. M. Bhattarai, R. P. Bonar-Law, A. P. Davis, B. A. Murray, J. Chem. Soc. Chem. Commun. 1992, 752; c) A. P. Davis, S. Menzer, J. J. Walsh, D. J. Williams, Chem. Commun. 1996, 453; d) K. M. Bhattarai, A. P. Davis, J. J. Perry, C. J. Walter, S. Menzer, D. J. Williams, J. Org. Chem. 1997, 62, 8463. Representative examples from other laboratories: e) Y. Aoyama, Y. Tanaka, S. Sugahara, J. Am. Chem. Soc. 1989, 111, 5397; f) Y. Kikuchi, Y. Tanaka, S. Sutaro, K. Kobayashi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 10302; g) R. Liu, W. C. Still, Tetrahedron Lett. 1993, 34, 2573; h) C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778. i) M. Inouye, T. Miyake, M. Furusyo, H. Nakazumi, J. Am. Chem. Soc. 1995, 117, 12416; j) G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139.
29. a) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596;
30. a) S. Anderson, U. Neidlein, V. Gramlich, F. Diederich, Angew. Chem. 1995, 107, 1722; Angew. Chem. Int. Ed. Engl. 1995, 34, 1596;
31. b) U. Neidlein, F. Diederich, Chem. Commun. 1996, 1493;
32. c) P. B. Savage, S. H. Gellman, J. Am. Chem. Soc. 1993, 115, 10448;
33. d) R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259;
34. e) T. Mizutani, T. Murakami, N. Matsumi, T. Kurahashi, H. Ogoshi, J. Chem. Soc. Chem. Commun. 1995, 1257. The receptors in references [6a-c] exploit strong hydrogen bonds to ionic centers, while those in references [6d,e] employ Zn-O interactions.
35. F. A. Quiocho, Pure Appl. Chem. 1989, 61, 1293.
36. 3 GB/SA solvation.
37. This unexpected direction of shift may be due to displacement of methanol by the carbohydrate, giving a structure in which not all NH groups are maximally hydrogen-bonded. Alternatively, a conformational change may take place, altering the position of the NH protons in relation to the arene rings.
38. At first sight it might be thought that, at fast exchange, all eight NH protons would be equivalent. However, the carbohydrate substrate lacks any element of symmetry, and therefore creates eight different NH environments on interaction with the receptor. Coalescence of these eight signals would require fast exchange between eight equivalent binding orientations. The symmetry of 1 allows only four such orientations, and the NH protons are therefore split into two groups of four.
39. 3OH (92:8) suggest that the carbohydrate protons experience upfeld shifts of about 0.2-0.3 ppm on complexation. These modest shifts might imply attachment to the exterior of 1, or might reflect competing shielding/deshielding effects from the arene rings defining the cavity.
40. 1H NMR titrations analyzed by HOSTEST 5.0. See: a) C. S. Wilcox in Frontiers in Supramolecular Chemistry and Photochemistry (Eds.: H.-J. Schneider, H. Dürr), VCH, Weinheim, 1990, p. 123.
41. Y. Tanaka, C. Khare, M. Yonezawa, Y. Aoyama, Tetrahedron Lett. 1990, 31, 6193.
42. Inverse micelles: N. Greenspoon, E. Wachtel, J. Am. Chem. Soc. 1991, 113, 7233; T. Kida, D. Furue, A. Masuyama, Y. Nakatsuji, I. Ikeda, Chem. Lett. 1996, 733. "Unimolecular inverse micelles": K. Kobayashi, F. Ikeuchi, S. Inaba, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 1105.
43. Inverse micelles: N. Greenspoon, E. Wachtel, J. Am. Chem. Soc. 1991, 113, 7233; T. Kida, D. Furue, A. Masuyama, Y. Nakatsuji, I. Ikeda, Chem. Lett. 1996, 733. "Unimolecular inverse micelles": K. Kobayashi, F. Ikeuchi, S. Inaba, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 1105.
44. Inverse micelles: N. Greenspoon, E. Wachtel, J. Am. Chem. Soc. 1991, 113, 7233; T. Kida, D. Furue, A. Masuyama, Y. Nakatsuji, I. Ikeda, Chem. Lett. 1996, 733. "Unimolecular inverse micelles": K. Kobayashi, F. Ikeuchi, S. Inaba, Y. Aoyama, J. Am. Chem. Soc. 1992, 114, 1105.
45. F. Franks, P.J. Lillford, G. Robinson, J. Chem. Soc. Faraday Trans. 1 1989, 85, 2417.