Synthetic hydrogen-bonding receptors for biologically essential monosaccharides

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 58, Issue 11, 2000, Pages 1077-1082

  Inouye, Masahiko ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 11144224667     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.58.1077     Document Type: Article

References (51)

1. General books: Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
2. Watson, J. D.; Hopkins, N. H.; Roberts, J. W.; Steitz, J. A.; Weiner, A. M. Molecular Biology of the Gene, 4th ed.; Benjamin: Menlo Park, 1987.
3. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Watson, J. D. Molecular Biology of the Cell, 3rd ed.; Garland: New York, 1994.
4. Lewin, B. Genes V; Oxford University Press: Oxford, 1994.
5. General books and recent reviews: Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; Freeman: New York, 1985.
6. Perutz, M. F. Mechanisms of Cooperatively and Allosteric Regulation in Proteins; Cambridge University Press: Cambridge, 1989.
7. Voet, D.; Voet, J. G. Biochemistry; Wiley: New York, 1990.
8. Branden C.; Tooze, J. Introduction to Protein Structure; Garland: New York, 1991.
9. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321.
10. Recent reviews: Hamilton, A. D. In Advances in Supramolecular Chemistry, Gokel, G. W., Ed.; JAI: Greenwich, 1990; Vol. 1; pp 1-64.
11. van Doom, A. R.; Verboom, W.; Reinhoudt, D. N. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI: Greenwich, 1993; Vol. 3; pp 159-206.
12. Zimmerman, S. C. Top. Curr. Chem. 1993, 165, 71.
13. Schneider, H.-J.; Mohammad-Ali, A. K. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 2, pp 91-95.
14. Ariga, K.; Kimitake, T. Acc. Chem. Res. 1998, 31, 371.
15. A recent review: Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1999, 38, 2978.
16. Inouye, M.; Ueno, M.; Kitao, T.; Tsuchiya, K. J. Am. Chem. Soc. 1990, 112, 8977.
17. Inouye, M. Coord. Chem. Rev. 1996, 148, 265.
18. Inouye, M.; Akamatsu, K.; Nakazumi, H. J. Am. Chem. Soc. 1997, 119, 9160.
19. Inouye, M.; Fujimoto, K.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 1452.
20. Inouye, M.; Hyodo, Y.; Nakazumi, H. J. Org. Chem. 1999, 64, 2704.
21. Inouye, M.; Itoh, M. S.; Nakazumi, H. J. Org. Chem. 1999, 64, 9393.
22. (a) Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416.
23. (b) Inouye, M.; Miyake, T.; Furusyo, M. J. Synth. Org. Chem. Jpn. 1996, 54, 311.
24. (c) Inouye, M.; Takahashi, K.; Nakazumi, H. J. Am. Chem. Soc. 1999, 121, 341.
25. (d) Inouye, M.; Chiba, J.; Nakazumi, H. J. Org. Chem. 1999, 64, 8170.
26. Schneider, H.-J.; Mohammad-Ali, A. K. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 2, pp 89-95.
27. Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778.
28. Coterón, J. M.; Hacket, F.; Schneider, H.-J. J. Org. Chem. 1996, 61, 1429.
29. Dela Rosa, M. A.; Velarde, E.; Guzman, A. Synth. Commun. 1990, 20, 2059.
30. Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444.
31. Anslyn, et al. reported the recognition of cyclohexanediol and triol by polyaza-clefts: Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. Tetrahedron Lett. 1990, 31, 7411.
32. Huang, C.-Y.; Cabell, L. A.; Lynch, V.; Anslyn, E. V. J. Am. Chem. Soc. 1992, 114, 1900.
33. Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778.
34. Ribose recognition as a pyranoside form was reported by Aoyama et al.: Aoyama, Y.; Yanagihara, R.; Fujimoto, T. J. Synth. Org. Chem. Jpn. 1994, 52, 572.
35. Aoyama, Y. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 2, pp 279-307.
36. Connors, K. A. Binding Constants; Wiley-Interscience: New York, 1987.
37. Bald, E.; Saigo, K.; Mukaiyama, T. Chem. Lett. 1975, 1163.
38. Benz, G. In Comprehensive Organic Synthesis; Trost, B. M. et al. Eds.; Pergamon: Oxford, 1991; Vol. 6, pp 381-417.
39. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M. et al. Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
40. Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J. Eds.; Wiley-VCH: Weinheim, 1998; pp 203-229.
41. Scott, W. J.; Peña, M. R.; Swärd, K.; Stoessel, S. J.; Stille, J. K. J. Org. Chem. 1985, 50, 2302.
42. A recent review for original Heck reaction: Bräse, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J. Eds.; Wiley-VCH: Weinheim, 1998; pp 99-166.
43. Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297.
44. Fredericks, J. R.; Hamilton, A. D. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier: Oxford, 1996; Vol. 9, pp 565.
45. Recently, Davis and Wareham reported a tricyclic polyamide receptor that shows a remarkable level of affinity for β-glucopyranoside: Davis, A. P.; Wareham, R. S. Angew. Chem., Int. Ed. 1998, 37, 2270.
46. Gerbeleu, N. V.; Arion, V. B.; Burgess, J. Template Synthesis of Macrocyclic Compounds; Wiley-VCH: Weinheim, 1999.
47. Other representative approaches for saccharide recognition: Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139.
48. Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259.
49. Mizutani, T.; Murakami, T.; Matsumi, N.; Kurahashi, T.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1995, 1257.
50. Anderson, S.; Neidlein, U.; Gramlich, V.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1995, 34, 1596.
51. James, T. D.; Samankumara Sandanayake, K. R. A.; Shinkai, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1911.