Abstract
Macrocylic conformation of permethylated cyclodextrins and the geometry of their inclusion complexes were examined on the basis of the X-ray data of three permethylated α-cyclodextrin complexes and two permethylated β-cyclodextrin complexes. The host macrocyclic ring is remarkably distorted owing to steric hindrance involving the methyl groups and the inability to form intramolecular hydrogen bonds. The guest molecules are included within the host cavity, but their position and orientation are quite different from those found in the corresponding cyclodextrin complexes.
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References
M. L. Bender and M. Komiyama,Cyclodextrin Chemistry, Springer-Verlag, Berlin (1978).
J. Szejtli,Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest (1982).
R. J. Bergeron, D. M. Pillor, G. Gibeily, and W. P. Roberts,Bioorg. Chem. 7, 263–271 (1978).
K. Harata,Bull. Chem. Soc. Jpn. 49, 2066–2072 (1976).
I. Tabushi, Y. Kiyosuke, T. Sugimoto, and K. Yamamura,J. Am. Chem. Soc. 100, 916–919 (1978).
W. Saenger, M. Noltemeyer, P. C. Manor, B. Hingerty, and B. Klar,Bioorg. Chem. 5, 187–195 (1976).
R. I. Gelb, L. M. Schwartz, B. Cardelino, H. S. Fuhrman, R. F. Johnson, and D. A. Laufer,J. Am. Chem. Soc. 103, 1750–1757 (1981).
D. W. Griffiths and M. L. Bender,Adv. Catal. 23, 209–261 (1973).
R. L. VanEtten, G. A. Clowes, J. S. Sebastian, and M. L. Bender,J. Am. Chem. Soc. 89, 3253–3262 (1967).
J. Emert and R. Breslow,J. Am. Chem. Soc. 97, 670–671 (1975).
I. Tabushi, K. Shimokawa, N. Shimizu, and K. FujitaJ. Am. Chem. Soc. 98, 7855–7856, (1976).
I. Tabushi,Acc. Chem. Res. 15, 66–72, (1982).
J. Boger, R. J. Corcoran, and J. M. Lehn,Helv. Chim. Acta 61, 2190–2218 (1978).
B. Casu and M. Reggiani,Carbohydr. Res. 76, 59–66 (1979).
J. Szejtli, A. Lipták, I. Jodál, P. Fügedi, P. Nánási, and A. NeszmélyiStarch/Stürke 32, 165–169 (1980).
K. Harata,Bull. Chem. Soc. Jpn. 48, 2409–2413 (1975).
K. Harata,Bull. Chem. Soc. Jpn. 50, 1416–1424 (1977).
K. Harata, K. Uekama, M. Otagiri, F. Hirayama, and H. Ogino,Bull. Chem. Soc. Jpn. 54, 1954–1959 (1981).
K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,Bull. Chem. Soc. Jpn. 55 407–410 (1982).
K. Harata, K. Uekama, M. Otagiri, F. Hirayama, and Y. Sugiyama,Bull. Chem. Soc. Jpn. 55, 3386–3389 (1982).
K. Harata, K. Uekama, M. Otagiri, and F. Hirayama,Bull. Chem. Soc. Jpn. 55, 3904–3910 (1982).
J. J. Stezowski, K. H. Jogun, E. Eckle, and K. Bartels,Nature 274, 617–619 (1978).
A. D. French and V. G. Murphy,Carbohydr. Res. 27, 391–406 (1973).
K. Harata,Bull. Chem. Soc. Jpn. 55 2315–2320 (1982).
K. Lindner and W. Saenger,Carbohydr. Res. 99, 103–115 (1982).
W. Saenger, R. K. McMullan, J. Fayos, and D. Mootz,Acta Crystallogr. Sect. B 30, 2019–2028 (1974).
P. C. Manor and W. Saenger,J. Am. Chem. Soc. 96, 3630–3639 (1974).
M. Czugler, E. Eckle, and J. J. Stezowski,J. Chem. Soc. Chem. Commun., 1981, 1291–1292.
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Harata, K., Uekama, K., Otagiri, M. et al. Conformation of permethylated cyclodextrins and the host-guest geometry of their inclusion complexes. Journal of Inclusion Phenomena 1, 279–293 (1984). https://doi.org/10.1007/BF00656762
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DOI: https://doi.org/10.1007/BF00656762