Sugar-sensing by chiral orientation of dimeric boronic-acid-appended porphyrins which show selectivity for glucose and xylose

Chemistry Letters

Volumn , Issue 1, 1996, Pages 77-78

  Arimori, Susumu ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030532805     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.77     Document Type: Article

References (18)

1. K. Tsukagoshi and S. Shinkai, J. Org. Chem., 56, 4089 (1991);
2. K. Kondo, Y. Shiomi, M. Saisho, T. Harada, and S. Shinkai, Tetrahedron, 48, 8239 (1992).
3. H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, Tetrahedron Lett., 34, 6273 (1993);
4. H. Murakami, T. Nagasaki, I. Hamachi, and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 975.
5. T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Angew. Chem. Int. Ed. Engl., 33, 2207 (1994);
6. T. D. James, K. R. A. S. Sandanayake, and S. Shinkai, Nature, 374, 345 (1995).
7. J. Yoon and A. W. Czarnik, J. Am. Chem. Soc., 114, 5874 (1992);
8. M.-F. Paugan and B. D. Smith, Tetrahedron Lett., 34, 3723 (1993).
9. Y. Nagai, K. Kobayashi, H. Toi, and Y. Aoyama, Bull. Chem. Soc. Jpn., 66, 2965 (1993).
10. For a comprehensive review see F. Ohseto, K. Nakashima, and S Shinkai, Yukagaku, 43, 845 (1994).
11. For sugar recognition by porphyrins using the hydrogen-bonding interaction see T. Mizutani, T. Murakami, N. Matsumi, T. Kurahashi, and H. Ogoshi, J. Chem. Soc., Chem. Commun., 1995, 1257.
12. T. Imada, H. Murakami, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 1557.
13. T. La, R. Richard, and G. M. Miskelly, Inorg. Chem., 33, 3159 (1994);
14. J. F. Lispskier and T. L. Tran-Thi, Inorg. Chem., 32, 722 (1993);
15. T. Shimizu and T. Iyoda, Chem. Lett., 1981, 853;
16. U. Hofstra, R. B. M. Koehorst, and T. J. Schaafsma, Chem. Phys. Lett., 130, 555 (1986).
17. S. Arimori, M. Takeuchi, and S. Shinkai, J. Chem. Soc., Chem. Commun., 1995, 961.
18. 5,10,15,20-Tetrakis(N-methyl-4-pyridiniurn)porphyrin tetratosylate (3) forms a 2:1 1-3 complex (evidenced by the continuous variation plot). Neither glucose nor xylose gave any CD-active species with the trimeric complex. The result also supports the view that the CD-active species with the dimeric 1·2 complexes stem from the bridging of two porphyrins by these monosaccharides.