Sugar sensing using chiral salen-Co(II) complexes

Tetrahedron

Volumn 55, Issue 31, 1999, Pages 9455-9468

  Mizuno, Toshihisa ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLOSE; BORONIC ACID DERIVATIVE; COBALT COMPLEX; FRUCTOSE; GLUCOSE; XYLOSE;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033618468     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00519-0     Document Type: Article

References (45)

1. (a) Rebek, Jr., J.; Marshall, L.; Wolak, L.; Parris, K.; Killoran, M.; Askew, B.; Nemeth, D. J. Am. Chem. Soc., 1985, 107, 7476.
2. (b) Rebek, Jr., J.; Nemeth, D. J. Am. Chem. Soc., 1986, 108 , 5637.
3. (c) Rebek, Jr., J.; Askew, B.; Killoran, M.; Nemeth, D.; Lin, F. T. J. Am. Chem. Soc., 1987, 109, 2426.
4. (d) Rebek, Jr., J. Angew. Chem., Int. Ed. Engl., 1990, 29, 245.
5. (e) Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc., 1987, 109, 5035.
6. (f) Chang, S. K.; Hamilton, A. D. J. Am. Chem. Soc., 1988, 110, 1318.
7. (g) Hamilton, A. D.; Pant, N. J. J. Chem. Soc., Chem. Commun., 1988, 765.
8. (h) Goswam, S.; Hamilton, A. D. J. Am. Chem. Soc., 1989, 111, 3425.
9. (i) Kelly, T. R.; Maguire, P. M. J. Am. Chem. Soc., 1987, 109, 6549.
10. (j) Kelly, T. R.; Zhao, C.; Bridger, G. J. J. Am. Chem. Soc., 1989, 111, 3744.
11. (k) Etter, M. C.; Paunto, T. W. J. Am. Chem. Soc., 1988, 110, 5896.
12. (l) Etter, M. C.; Adsmond, D. A. J. Am. Chem. Soc., 1990, 112, 4549.
13. (m) Bell, T. W.; Liu, J. J. Am. Chem. Soc., 1988, 110, 3673.
14. (n) Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc., 1988, 110, 634.
15. (o) Tanaka, Y.; Ubukata, Y;. Aoyama, Y. Chem. Lett., 1988, 1905.
16. (p) Kano, K.; Yoshiyasu, K.; Hashimoto, S. J. Chem. Soc., Chem. Commun., 1988, 801.
17. (a) Wulff, G.; Vietmeier, J.; Poll, H. G. Makromol. Chem., 1987, 188, 731.
18. (b) Wulff, G.; Poll, H. G. Makromol. Chem., 1987, 188, 741.
19. (a) Kondo, K.; Shiomi, Y.; Saisho, M.; Harada, T.; Shinkai, S. Tetrahedron, 1992, 48, 8239.
20. (b) Tsukagoshi, K.; Shinkai, S. J. Org. Chem., 1991, 56, 4089.
21. (c) Shiomi, Y.; Saisho, M.; Tsukagoshi, K.; Shinkai, S. J. Chem. Soc., Perkin Trans. 1, 1993, 2111.
22. (d) Shiomi, Y.; Kondo, K.; Saisho, M.; Harada, T.; Tsukagoshi, K.; Shinkai, S. Supramol. Chem., 1993, 2, 11.
23. Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc., 1992, 114, 5874.
24. For comprehensive reviews on boronic-acid-based sugar receptors see (a) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Supramol. Chem., 1995, 6, 141.
25. (b) James, T. D.; Linnane, P.; Shinkai, S. J. Chem. Soc., Chem. Commun. (Future Article), 1996, 281.
26. (c) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1910.
27. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc., 1995, 117, 8982.
28. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Angew. Chem., Int. Ed. Engl., 1994, 33, 2207; James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc., 1995, 117, 8982.
29. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature, 1995, 374, 345.
30. Takeuchi, M.; Yoda, S.; Imada, T.; Shinkai, S. Tetrahedron, 1997, 53, 8335.
31. Ori, A.; Shinkai, S. J. Chem. Soc., Chem. Commun., 1995, 1771.
32. For recent reviews for the catalytic reactions mediated by salen-Co(II) complexes, see (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science, 1997, 277, 936.
33. (b) Fukuda, T.; Katsuki, T. Tetrahedron Lett., 1997, 38, 3435., Idem Tetrahedron, 1997, 53, 7201 and Yamashita, Y.; Katsuki, T. Synlett., 1995, 825.
34. (b) Fukuda, T.; Katsuki, T. Tetrahedron Lett., 1997, 38, 3435., Idem Tetrahedron, 1997, 53, 7201 and Yamashita, Y.; Katsuki, T. Synlett., 1995, 825.
35. (b) Fukuda, T.; Katsuki, T. Tetrahedron Lett., 1997, 38, 3435., Idem Tetrahedron, 1997, 53, 7201 and Yamashita, Y.; Katsuki, T. Synlett., 1995, 825.
36. (c) Das, B. C.; Iqbal, J. Tetrahedron Lett., 1997, 38, 2903.
37. (d) Föster, S.; Rieker, A. J. Org. Chem., 1996, 61, 3320 and cited therein.
38. For an example of electrochemical sensing, see Ref. 9.
39. For Co(II)-Co(III) interconversion coupled to sugar sensing, see (a) Mizuno, T.; Takeuchi, M.; Hamachi, I.; Nakashima, K.; Shinkai, S. Chem. Commun., 1997, 1793 and (b) Idem J. Chem. Soc., Perkin Trans. 2, 1998, 2281.
40. For Co(II)-Co(III) interconversion coupled to sugar sensing, see (a) Mizuno, T.; Takeuchi, M.; Hamachi, I.; Nakashima, K.; Shinkai, S. Chem. Commun., 1997, 1793 and (b) Idem J. Chem. Soc., Perkin Trans. 2, 1998, 2281.
41. Pfeiffer, P.; Breith, E.; Lübbe, E.; Tamaki, T. Ann., 1993, 503, 84.
42. Pearson, D. E.; Wysong, R. D.; Breder, C. V. J. Org. Chem., 1967, 32, 2358.
43. Busetto, C.; Cariati, F.; Fusi, A.; Gullotti, M.; Morazzioni, F.; Pasini, A.; Ugo, R. J. Chem. Soc. Dalton Trans., 1973, 754.
44. Suenaga, H.; Mikami, M.; Sandanayake, K. R. A. S.; Shinkai, S. Tetrahedron, 1995, 36, 4825.
45. Norrild, J. C.; Eggart, H. J. Chem Soc., Perkin Trans. 2, 1996, 12, 2583.