Inside-outside isomerism of β-cyclodextrin covalently linked with a naphthyl group

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2750-2751

  McAlpine, Shelli R ^a   Garcia Garibay, Miguel A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ISOMERISM; NUCLEAR MAGNETIC RESONANCE;

EID: 0029887670     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953061j     Document Type: Article

References (34)

1. (a) Ueno, A.; Osa, T. In Photochemistry in Organized and Constrained Media: Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; pp 739-782.
2. (b) Kalyanasundaram, K. Photochemistry in Microheterogeneous Systems; Academic Press: New York, 1987.
3. (c) Ramamurthy, V.; Eaton, D. F. Acc. Chem. Res. 1988, 21, 300-306.
4. (a) Hamada, F.; Fukushima, M.; Osa, T.; Ueno, A. Makromol. Chem., Rapid Commun. 1993, 14, 279-286.
5. (b) Hamada, F.; Fukushima, M.; Osa, T.; Ikeda, H.; Toda, F.; Ueno, A. Makromol. Chem., Rapid Commun. 1993, 14, 287-291.
6. (c) Hamasaki, K.; Ueno, A.; Toda, F. J. Chem. Soc., Chem. Commun. 1993, 331-333
7. (d) Hamasaki, K.; Ikeda, H.; Nakamura, A.; Ueno, A.; Toda, F ; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035-5040.
8. Arad-Yellin, R ; Green, B. S. Nature 1994, 371, 320-322.
9. (a) Ikeda, T.; Yoshida, K.; Schneider, H. J. Am. Chem. Soc. 1995, 117, 1453-1454.
10. (b) Hamasaki, K.; Ikeda, H., Nakamura, A.; Ueno, A.; Toda, F.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035-5040.
11. (a) Seliskar, C. J.; Brand, L. J. Am. Chem. Soc. 1971, 93, 5405-5414.
12. (b) Seliskar, C. J.; Brand, L. J. Am. Chem. Soc. 1971, 93, 5414-5420.
13. (c) DeToma, R. P.; Easter, J. H.; Brand, L. J. Am. Chem. Soc. 1976, 98, 5001-5007.
14. The preparation and properties of naphthyldiazomethane have been reported by several authors: (a) McMahon, R. J . Albrecht, S. W. J. Am. Chem. Soc 1993, 115, 855-859. (b) Platz, M. S.; Maloney, V. J Phys. Org. Chem. 1990, 3, 135-138. (c) Griffin, K. H. J. Am. Chem. Soc. 1987, 109, 4919-4926.
15. The preparation and properties of naphthyldiazomethane have been reported by several authors: (a) McMahon, R. J . Albrecht, S. W. J. Am. Chem. Soc 1993, 115, 855-859. (b) Platz, M. S.; Maloney, V. J Phys. Org. Chem. 1990, 3, 135-138. (c) Griffin, K. H. J. Am. Chem. Soc. 1987, 109, 4919-4926.
16. The preparation and properties of naphthyldiazomethane have been reported by several authors: (a) McMahon, R. J . Albrecht, S. W. J. Am. Chem. Soc 1993, 115, 855-859. (b) Platz, M. S.; Maloney, V. J Phys. Org. Chem. 1990, 3, 135-138. (c) Griffin, K. H. J. Am. Chem. Soc. 1987, 109, 4919-4926.
17. Inclusion complexes were prepared by addition of concentrated methanolic solutions of freshly prepared 1 to dilute solutions of β-cyclodextrin in a 1:1 molar ratio. Photolyses were carried out immediately with a 400 W Hanovia lamp (λ > 300 nm. Pyrex filter).
18. (a) Smith, S. H., Forrest, S. M.; Williams, D. C . Acquavella, M F.; Abelt, C. J. Carbohydr. Res. 1992, 230, 289-297.
19. (b) Abelt, C. J.; Lokey, J S ; Smith, S. H. Carbohydr. Res. 1989, 192, 119-130.
20. (c) Abelt, C. J.; Pleier, J. J. Org. Chem. 1988, 53, 2159-2162. For a related example, see: Brinker, U., Buchkremer, R.; Rosenberg, M., Polkis, M. D.; Orlando, M.; Gross, M. L Angew. Chem., Int. Ed. Engl. 1993, 32, 1344.
21. (c) Abelt, C. J.; Pleier, J. J. Org. Chem. 1988, 53, 2159-2162. For a related example, see: Brinker, U., Buchkremer, R.; Rosenberg, M., Polkis, M. D.; Orlando, M.; Gross, M. L Angew. Chem., Int. Ed. Engl. 1993, 32, 1344.
22. For reviews, see: (a) Moss, R. A., Jones, M. J. Carbenes; Wileylnterscience: New York, 1985. (b) Kirmse, W. Carbene Chemistry, 2nd ed., Academic Press, New York, 1971.
23. For reviews, see: (a) Moss, R. A., Jones, M. J. Carbenes; Wileylnterscience: New York, 1985. (b) Kirmse, W. Carbene Chemistry, 2nd ed., Academic Press, New York, 1971.
24. Bayley, H. In Photogenerated Reagents in Bialogy and Molecular Biolagy. Work, T. S., Burdon, R. H. Eds.; Elsever: Amsterdam, 1983,
25. 1H NMR spectra run in DMSO. as reported by Abelt et al. in ref 8a.
26. (a) Schneider, H.-J.; Blatter, T.; Simova, S. J. Am. Chem. Soc. 1991, 113, 1996-2000.
27. (b) Hamai, S. J. Phys. Chem. 1995, 99, 12109-12144.
28. The effect of β-cyclodextrin on the fluorescence of several noncovalent and covalent naphthalene derivatives has been analyzed: (a) Encinas, M. V ; Lissi, E. A : Rufs, A. M Photochem. Photobiol. 1993, 57, 603-608 (b) Fujita, K.; Tahara, T : Koga, T.; Imoto, T. Chem. Soc. Jpn 1987, 300-305. (c) Ueno, A.; Moriwaki, F., Osa, T ; Hamada, F.; Murai. K. Bull. Chem. Soc Jpn. 1986, 59, 465-470
29. The effect of β-cyclodextrin on the fluorescence of several noncovalent and covalent naphthalene derivatives has been analyzed: (a) Encinas, M. V ; Lissi, E. A : Rufs, A. M Photochem. Photobiol. 1993, 57, 603-608 (b) Fujita, K.; Tahara, T : Koga, T.; Imoto, T. Chem. Soc. Jpn 1987, 300-305. (c) Ueno, A.; Moriwaki, F., Osa, T ; Hamada, F.; Murai. K. Bull. Chem. Soc Jpn. 1986, 59, 465-470
30. The effect of β-cyclodextrin on the fluorescence of several noncovalent and covalent naphthalene derivatives has been analyzed: (a) Encinas, M. V ; Lissi, E. A : Rufs, A. M Photochem. Photobiol. 1993, 57, 603-608 (b) Fujita, K.; Tahara, T : Koga, T.; Imoto, T. Chem. Soc. Jpn 1987, 300-305. (c) Ueno, A.; Moriwaki, F., Osa, T ; Hamada, F.; Murai. K. Bull. Chem. Soc Jpn. 1986, 59, 465-470
31. Several studies have addressed the fluorescence properties of TNS complexed with β-cyclodextrin: (a) Kondo, H.; Nakatan, H., Hiromi, K. J. Biochem 1976, 79, 393-405. (b) Nakamura, A.; Saitoh, K.; Toda, F. Chem. Lett 1989, 2209-2212 (c) Schneider, H.-J., Blatter, T.; Simova, S. J. Am. Chem. Sov. 1991, 113, 1996-2000 and references therein
32. Several studies have addressed the fluorescence properties of TNS complexed with β-cyclodextrin: (a) Kondo, H.; Nakatan, H., Hiromi, K. J. Biochem 1976, 79, 393-405. (b) Nakamura, A.; Saitoh, K.; Toda, F. Chem. Lett 1989, 2209-2212 (c) Schneider, H.-J., Blatter, T.; Simova, S. J. Am. Chem. Sov. 1991, 113, 1996-2000 and references therein
33. Several studies have addressed the fluorescence properties of TNS complexed with β-cyclodextrin: (a) Kondo, H.; Nakatan, H., Hiromi, K. J. Biochem 1976, 79, 393-405. (b) Nakamura, A.; Saitoh, K.; Toda, F. Chem. Lett 1989, 2209-2212 (c) Schneider, H.-J., Blatter, T.; Simova, S. J. Am. Chem. Sov. 1991, 113, 1996-2000 and references therein
34. Kondo, H., Nakatani, H.; Hiromi, K. J Biochem. 1976, 79, 393-405