Abstract
Starting from regiospecific prim, prim A, B-disulfonate capped cyclodextrin, a series of the A, B-difunctional cyclodextrins were prepared. Typical examples are A(B)-amino-B(A)-carboxy-ß-cyclodextrins and A(B)-amino-B(A)-B6-cyclodextrins. These artificial compounds have remarkable characteristics of enzymes or receptors chiral specificity, guest shape and size selectivity, acceleration and turn-over. Activities of artificial racemase, artificial aminotransferase, artificial amino acid receptors will be discussed.
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References
Matsui, Y., Yokoi, T., and Mochida, K., Chem, Lett. p. 1037 (1976).
Tabushi, I., Shimizu, N., and Yamamura, K., J. Am. Chem. Soc. 99, 7100 (1977)
Tabushi, I., Shimizu, N., and Yamamura, K., Int. Congr. Pure Appl. Chem., 26th I, 44 (1977). (Abstr.)
Siegel, B., Pinter, A., and Breslow, R., J. Am. Chem. Soc. 99, 2509, (1977).
Eiki, T., and Tagaki, W., Chem. Lett. p. 1063 (1980).
Siegel, B., J. Inorg. Nucl. Chem. 41, 609 (1979).
Breslow, R., Hammond, M., and Laner, M., J. Am. Chem. Soc. 102, 5402 (1980).
Tabushi, I., Kuroda, Y., and Shimokawa, K., J. Am. Chem. Soc., 101, 1614 (1979).
Tabushi, I., and Shimokawa, K., J. Am. Chem. Soc. 102, 5402., 1980.
Iwakura, Y., Uno, K., Toda, F. and Bender, M. L., J. Am. Chem. Soc. 97, 4432 (1975).
Kitaura, Y., and Bender, M. L. Bioorg. Chem. 4, 219, 237, 1975.
Tabushi, I., Kuroda, Y., and Sakata, Y., Heterocycles 15, 815, (1981).
Matsui, Y., and Okimoto, A., Bull. Chem. Soc. Jpn. 51, 3030 (1978)
Breslow, R., and Overman, L. E., J. Am. Chem. Soc. 92, 1075 (1970).
A Part of the description is drafted from the following article. Tabushi, I., and Kuroda, Y., ‘Cyclodextrins and Cyclophanes as Enzyme Models’ in ‘Advances in Catalysis’, Dley, D. D., Pines, H. and Weisz, P. B. Eds. 32, 417, Academic Press (1983). Academic Press (1983).
Tabushi, I., Shimokawa, K., Shimizu, N., Shirakata, H., and Fujita, K., J. Am. Chem. Soc. 98, 7855 (1978).
Tabushi, I., Kuroda, Y., Yokota, K. and Yuan, L. C., ibid. 13, 711 (1981).
Tabushi, I., Yuan, L. C., Shimokawa, K., Mizutani, T. and Kuroda, Y., Tet. Lett. 22, 2273 (1981).
Tabushi, I. and Yuan, L. C., J. Am. Chem. Soc. 103, 3574 (1981).
Tabushi, I., Kuroda, Y. and Yokota, K., Tet. Lett. 23, 4601 (1982).
Tabushi, I., Yamamura, K., Nabeshima, T., J. Am. Chem. Soc. 106, 5267 (1984).
Tabushi, I., Nabeshima, T., Fujita, K., Matunaga, A., and Imoto, T., J. Org. Chem., in press: For review, see Tabushi, I., Acc. Chem. Res. 15, 66 (1982).
Tabushi, I., Kuroda, Y., and Mochizuki, A., J. Am. Chem. Soc. 102, 1152 (1980).
Breslow, R., Hammond, M., and Lauer, M., J. Am. Chem. Soc. 102 421 (1983).
Breslow, R., and Czarnik, A. W., ibid. 105, 1390 (1983).
Zimmerman, S. C., and Breslow, R., ibid. 106, 1490 (1984).
A part of the description is drafted from the following article. Tabushi, I., Kuroda, Y., Yamada, M., Higashimura, H., and Breslow, R., submitted to J. Am. Chem. Soc.
Tabushi, I. and Kuroda, Y., unpublished result
The present yield of 6 is neither corrected for the conversion in acylation (which may not be exactly the same for D- and L-amino acid) nor the extraction efficiency.
Tabushi, I., Shimokawa, K., and Fujita, K., J. Am. Chem. Soc. 99, 1527 (1977).
Tabushi, I., Kuroda, Y. and Shimokawa, K., ibid. 101, 1614 (1979).
Boger, J., Brenner, P. G. and Knowls, J. R., Ibid. 101, 7631 (1979).
Tabushi, I., Kuroda, Y. and Mizutani, T., Tetrahedron 40, 545 (1984).
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© 1986 D. Reidel Publishing Company, Dordrecht, Holland
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Tabushi, I. (1986). Chiral, Size and Shape Recognition of Guests by Modified Cyclodextrin. In: Setton, R. (eds) Chemical Reactions in Organic and Inorganic Constrained Systems. NATO ASI Series, vol 165. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4582-1_1
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DOI: https://doi.org/10.1007/978-94-009-4582-1_1
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