Computer-guided design in molecular recognition: Design and synthesis of a glucopyranose receptor

Angewandte Chemie - International Edition

Volumn 40, Issue 9, 2001, Pages 1714-1718

  Yang, Wei ^a   He, Huan ^a   Drueckhammer, Dale G ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Boron; Molecular modeling; Molecular recognition; Receptors; Sensors

Indexed keywords

FLUORESCENCE; FRUCTOSE; MOLECULES;

MOLECULAR RECOGNITION;

GLUCOSE;

GLUCOPYRANOSIDE;

ARTICLE; BINDING AFFINITY; BIOSENSOR; COMPUTER MODEL; CYCLIZATION; DISSOCIATION CONSTANT; ENANTIOMER; GEOMETRY; MOLECULAR RECOGNITION; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION; STRUCTURE ANALYSIS;

EID: 0035805381     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010504)40:9<1714::AID-ANIE17140>3.0.CO;2-F     Document Type: Article

References (48)

1. A. W. Czarnik, Chem. Biol. 1995, 2, 423-428.
2. R. Breslow, Acc. Chem. Res. 1995, 28, 146-153; P. Tecilla, V. Jubian, A. D. Hamilton, Tetrahedron 1995, 51, 435-438.
3. R. Breslow, Acc. Chem. Res. 1995, 28, 146-153; P. Tecilla, V. Jubian, A. D. Hamilton, Tetrahedron 1995, 51, 435-438.
4. E. V. Anslyn, A. Metzger, Angew. Chem. 1998, 110, 682-684; Angew. Chem. Int. Ed. 1998, 37, 649-652; C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
5. E. V. Anslyn, A. Metzger, Angew. Chem. 1998, 110, 682-684; Angew. Chem. Int. Ed. 1998, 37, 649-652; C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
6. E. V. Anslyn, A. Metzger, Angew. Chem. 1998, 110, 682-684; Angew. Chem. Int. Ed. 1998, 37, 649-652; C.-Y. Huang, L. A. Cabell, E. V. Anslyn, J. Am. Chem. Soc. 1994, 116, 2778-2792.
7. G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139-11140; T. W. Bell, Z. Hou, Y. Luo, M. G. B. Drew, E. Chapoteau, B. P. Czech, A. Kumar, Science 1995, 269, 671.
8. G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11139-11140; T. W. Bell, Z. Hou, Y. Luo, M. G. B. Drew, E. Chapoteau, B. P. Czech, A. Kumar, Science 1995, 269, 671.
9. G. Lauri, P. A. Bartlett, J. Comput. Aided Mol. Des. 1994, 8, 51-66.
10. P. A. Bartlett, G. T. Shea, S. J. Telfer, S. Waterman in Molecular Recognition: Chemical and Biological Problems (Ed.: S. M. Roberts), Royal Society of Chemistry, London, 1989, pp. 182-196; P. A. Bartlett, F. A. Etzkorn, T. Guo, G. Lauri, K. Liu, M. Lipton, B. P. Morgan, G. T. Shea in Chemistry at the Frontiers of Medicine, Proceedings of the Robert A. Welch Foundation Conference on Chemical Research XXXV (Houston TX), 1992, pp. 45-68.
11. P. A. Bartlett, G. T. Shea, S. J. Telfer, S. Waterman in Molecular Recognition: Chemical and Biological Problems (Ed.: S. M. Roberts), Royal Society of Chemistry, London, 1989, pp. 182-196; P. A. Bartlett, F. A. Etzkorn, T. Guo, G. Lauri, K. Liu, M. Lipton, B. P. Morgan, G. T. Shea in Chemistry at the Frontiers of Medicine, Proceedings of the Robert A. Welch Foundation Conference on Chemical Research XXXV (Houston TX), 1992, pp. 45-68.
12. J. P. Lorand, J. O. Edwards, J. Org. Chem. 1959, 24, 769-774.
13. J. Yoon, A. W. Czarnik, J. Am. Chem. Soc. 1992, 114, 5874-5875; T. D. James, K. R. A. S. Sandanayake, S. Shinkai, J. Chem. Soc. Chem. Commun. 1994, 477-478.
14. J. Yoon, A. W. Czarnik, J. Am. Chem. Soc. 1992, 114, 5874-5875; T. D. James, K. R. A. S. Sandanayake, S. Shinkai, J. Chem. Soc. Chem. Commun. 1994, 477-478.
15. H. Suenaga, M. Mikami, K. R. A. S. Sandanayake, S. Shinkai, Tetrahedron Lett. 1995, 36, 4825-4828.
16. P. Linnane, T. D. James, S. Imazu, S. Shinkai, Tetrahedron Lett. 1995, 36, 8833-8834; K. R. A. S. Sandanayake, T. D. James, S. Shinkai, Chem. Lett. 1995, 503-504; T. D. James, P. Linnane, S. Shinkai, Chem. Commun. 1996, 281-288. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347.
17. P. Linnane, T. D. James, S. Imazu, S. Shinkai, Tetrahedron Lett. 1995, 36, 8833-8834; K. R. A. S. Sandanayake, T. D. James, S. Shinkai, Chem. Lett. 1995, 503-504; T. D. James, P. Linnane, S. Shinkai, Chem. Commun. 1996, 281-288. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347.
18. P. Linnane, T. D. James, S. Imazu, S. Shinkai, Tetrahedron Lett. 1995, 36, 8833-8834; K. R. A. S. Sandanayake, T. D. James, S. Shinkai, Chem. Lett. 1995, 503-504; T. D. James, P. Linnane, S. Shinkai, Chem. Commun. 1996, 281-288. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347.
19. P. Linnane, T. D. James, S. Imazu, S. Shinkai, Tetrahedron Lett. 1995, 36, 8833-8834; K. R. A. S. Sandanayake, T. D. James, S. Shinkai, Chem. Lett. 1995, 503-504; T. D. James, P. Linnane, S. Shinkai, Chem. Commun. 1996, 281-288. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Nature 1995, 374, 345-347.
20. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922.
21. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922.
22. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1994, 106, 2287-2289; Angew. Chem. Int. Ed. Engl. 1994, 33, 2207-2209; T. D. James, K. R. A. S. Sandanayake, R. Iguchi, S. Shinkai, J. Am. Chem. Soc. 1995, 117, 8982-8987.
23. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1994, 106, 2287-2289; Angew. Chem. Int. Ed. Engl. 1994, 33, 2207-2209; T. D. James, K. R. A. S. Sandanayake, R. Iguchi, S. Shinkai, J. Am. Chem. Soc. 1995, 117, 8982-8987.
24. T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1994, 106, 2287-2289; Angew. Chem. Int. Ed. Engl. 1994, 33, 2207-2209; T. D. James, K. R. A. S. Sandanayake, R. Iguchi, S. Shinkai, J. Am. Chem. Soc. 1995, 117, 8982-8987.
25. K. Tsukagoshi, S. Shinkai, J. Org. Chem. 1991, 56, 4089-4091.
26. M. Bielecki, H. Eggert, J. C. Norrild, J. Chem. Soc. P2 1999, 449-455.
27. H. Eggert, J. Frederiksen, C. Morin, J. C. Norrild, J. Org. Chem. 1999, 64, 3846-3852.
28. C. R. Cooper, T. D. James, Chem. Lett. 1998, 883-884.
29. D. A. Gough, J. C. Armour, Diabetes 1995, 44, 1005-1009. R. J. McNichols, G. L. Cote, J. Biomed. Opt. 2000, 5, 15-16.
30. D. A. Gough, J. C. Armour, Diabetes 1995, 44, 1005-1009. R. J. McNichols, G. L. Cote, J. Biomed. Opt. 2000, 5, 15-16.
31. G. T. Morin, M.-F. Paugam, M. P. Hughes, B. D. Smith, J. Org. Chem. 1994, 59, 2724-2728.
32. C. J. Cramer, D. G. Truhlar, Science 1992, 26, 213-217; all calculations were carried out using the Gaussian 98 suite of programs: Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Avala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
33. C. J. Cramer, D. G. Truhlar, Science 1992, 26, 213-217; all calculations were carried out using the Gaussian 98 suite of programs: Gaussian 98 (Revision A.7), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Avala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
34. S. S. Lele, N. G. Savant, S. Sethna, J. Org. Chem. 1960, 25, 1713-1716.
35. D. I. Ivanova, S. V. Eremin, V. I. Shvets, Tetrahedron 1996, 52, 9581-9588.
36. W. Hao, Y. Zhang, T. Ying, P. Lu, Synth. Commun. 1996, 26, 2421-2427.
37. 14 was prepared by reaction of 2-butyn-1,4-diol with 1.0 equiv tert-butyldimethylsilyl chloride and imidazole to form the mono-TBS protected derivative followed by reaction with triphenylphosphane and carbon tetrabromide.
38. A. Padwa, F. R. Kinder, J. Org. Chem. 1993, 58, 21-28; T. R. Hoye, C. J. Dinsmore, D. S. Johnson, P. F. Korkowski, J. Org. Chem. 1990, 55, 4518-4520.
39. A. Padwa, F. R. Kinder, J. Org. Chem. 1993, 58, 21-28; T. R. Hoye, C. J. Dinsmore, D. S. Johnson, P. F. Korkowski, J. Org. Chem. 1990, 55, 4518-4520.
40. T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508-7510.
41. A. Giroux, Y. Han, P. Prasit, Tetrahedron Lett. 1997, 38, 3841-3844; T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, Tetrahedron Lett. 1997, 38, 3447-3450.
42. A. Giroux, Y. Han, P. Prasit, Tetrahedron Lett. 1997, 38, 3841-3844; T. Ishiyama, Y. Itoh, T. Kitano, N. Miyaura, Tetrahedron Lett. 1997, 38, 3447-3450.
43. J. E. McMurry, D. D. Miller, J. Am. Chem. Soc. 1983, 105, 1660-1661.
44. J. E. McMurry, T. Lectka, J. G. Rico, J. Org. Chem. 1989, 54, 3748-3749.
45. 1H NMR analysis.
46. Computer-based modeling also predicts that glucofuranose should not form a stable complex with both boronic acid groups of 7.
47. rel - 1)/Δε using Origin 5.0. The curves of Figure 2 were generated using B-spline fitting.
48. [8]