Molecular recognition of carbohydrates by zinc porphyrins: Lewis acid/Lewis base combinations as a dominant factor for their selectivity

Journal of the American Chemical Society

Volumn 119, Issue 38, 1997, Pages 8991-9001

  Mizutani, Tadashi ^a   Kurahashi, Takuya ^a   Murakami, Takeshi ^a   Matsumi, Noriyoshi ^a   Ogoshi, Hisanobu ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; ZINC COMPLEX;

ARTICLE; BINDING AFFINITY; CARBOHYDRATE ANALYSIS; CIRCULAR DICHROISM; COMPLEX FORMATION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0030763841     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9713183     Document Type: Article

References (37)

1. (a) Aoyama, Y.; Tanaka, Y.; Sugahara, S. J. Am. Chem. Soc. 1989, 111, 5397.
2. (b) Kurihara, K.; Ohto, K.; Tanaka, Y.; Aoyama, Y.; Kunitake, T. J. Am. Chem. Soc. 1991, 113, 444.
3. Bhattarai, K. M.; Bonar-Law, R. P.; Davis, A. P.; Murray, B. A. J. Chem. Soc., Chem. Commun. 1992, 752.
4. Liu, R.; Still, W. C. Tetrahedron Lett. 1993, 34, 2573.
5. (a) Murakami, H.; Nagasaki, T.; Hamachi, I.; Shinkai, S. Tetrahedron Lett. 1993, 34, 6273.
6. (b) James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. Nature 1995, 374, 345.
7. (c) James, T. D.; Sandanayake, K. R. A. S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982.
8. (d) Takeuchi, M.; Imada, T.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 10658.
9. Huang, C.-Y.; Cabell, L. A.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2778.
10. Eliseev, A. V.; Schneider, H.-J. J. Am. Chem. Soc. 1994, 116, 6081.
11. Das, G.; Hamilton, A. D. J. Am. Chem. Soc. 1994, 116, 11139.
12. Bonar-Law, R. P.; Sanders, J. K. M. J. Am. Chem. Soc. 1995, 117, 259.
13. Jimenez-Barbero, J.; Junquera, E.; Martin-Pastor, M.; Sharma, S.; Vicent, C.; Penades, S. J. Am. Chem. Soc. 1995, 117, 11198.
14. Inouye, M.; Miyake, T.; Furusyo, M.; Nakazumi, H. J. Am. Chem. Soc. 1995, 117, 12416.
15. Weis, W. I.; Drickamer, K.; Hendrickson, W. A. Nature 1992, 360, 127.
16. For preliminary accounts of this work, see: Mizutani, T.; Murakami, T.; Matsumi, N.; Kurahashi, T.; Ogoshi, H. J. Chem. Soc., Chem. Commun. 1995, 1257.
17. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
18. Owing to the small changes in absorbance in visible spectra, the precise determination of binding constants was difficult.
19. Johnson, C. E. J.; Bovey, F. A. J. Chem. Phys. 1958, 29, 1012.
20. Weis, W. I.; Drickamer, K.; Hendrickson, W. A. Nature 1992, 360, 127.
21. Mizutani, T.; Ema, T.; Yoshida, T.; Kuroda, Y.; Ogoshi, H. Inorg. Chem. 1993, 32, 2072.
22. Mizutani, T.; Ema, T.; Yoshida, T.; Renne, T.; Ogoshi, H. Inorg. Chem. 1994, 33, 3558.
23. (a) Miller, D. M., III.; Olson, J. S.; Pflugrath, J. W.; Quiochio, F. A. J. Biol. Chem. 1980, 255, 2465.
24. (b) Miller, D. M., III.; Olson, J. S.; Pflugrath, J. W.; Quiochio, F. A. J. Biol. Chem. 1983, 258, 13665.
25. (c) Bourne, Y.; Rouge, P.; Cambillau, C. J. Biol. Chem. 1990, 265, 18161.
26. To examine how ligand aggregation affects the dependence of K on additive concentration, we compared the behaviors of 1 and 3. Even though the binding constants were determined in the same concentration range of β-Gal, the binding constant between 3 and β-Gal increased while that between 1 and β-Gal simply decreased with increasing tert-butyl alcohol concentration, suggesting that the effects of tert-butyl alcohol cannot be ascribed to the dissolution of aggregate of β-Gal. The increased CD band by the addition of tert-butyl alcohol to the 3-β-Glc complex also indicates that the effects of additives were due to the interaction between the additive and the complex.
27. Gaunitz, S.; Schwarz, H.; Bohlmann, F. Tetrahedron 1975, 31, 185.
28. Aoyama, Y.; Kamohara, T.; Yamagishi, A.; Toi, H.; Ogoshi, H. Tetrahedron Lett. 1987, 28, 2143.
29. Mizutani, T.; Murakami, T.; Kurahashi, T.; Ogoshi, H. J. Org. Chem. 1996, 61, 539.
30. Matsumura, S.; Imai, K.; Yoshikawa, S.; Kawada, K.; Uchibori, T. J. Am. Oil Chem. Soc. 1990, 67, 996.
31. Kaur, K. J.; Hindsgaul, O. Glycoconjugate J. 1991, 8, 90.
32. Konradsson, P.; Roberts, C.; Fraser-Reid, B. Recl. Trav. Chim. Pays-Bas 1991, 110, 23.
33. Rosevear, P.; VanAken, T.; Baxter, J.; Ferguson-Miller, S. Biochemistry 1980, 19, 4108.
34. Albert, R.; Dax, K.; Pleschko, R.; Stutz, A. E. Carbohydr. Res. 1985, 137, 282.
35. Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647.
36. Boger, D. L.; Teramoto, S.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7344.
37. Hanessian, S.; Liak, T. J.; Vanasse, B. Synthesis 1981, 396.