Abstract
The optical resolution of α-amino acid was studied using chiral poly(crown ether)s 2 and 5. The former was prepared from cyclopolymerization of 1,3;4,6-di-O-benzylidene-2,5-bis-O-[2-(2-vinyloxyethoxy)ethyl]-D-mannitol (1), and the latter was obtained from copolymerization of acrylonitrile and macromonomer 4 synthesized through the polymerization of 1 with 2-vinyloxyethyl methacrylate in the presence of hydrogen iodide/iodine. The optical resolution of racemic α-amino acid methyl esters through bulk chloroform containing polymer 2 from one aqueous solution to another was examined. The faster moving enantiomer was the L-isomer, which agreed with the result in the one-plate extraction experiment. On the other hand, the column packed with chiral polymer 2 gave an eluent containing a mixture enriched in the D-isomer when being used for resolution of racemic α-amino acid methyl ester. The D-isomer permeated preferentially through the membrane prepared from copolymer 5 as well. The L-isomer which forms the more stable complex is easily absorbed by the stationary phases, resulting in an excess of the D-isomer in the final mobil phases.
Similar content being viewed by others
Article PDF
References
K. Yokota, M. Matsumura, K. Yamaguchi, and Y. Takada, Makromol. Chem., Rapid Commun., 4, 721 (1983).
T. Kakuchi and K. Yokota, Makromol. Chem., Rapid Commun., 6, 551 (1985).
T. Kakuchi, H. Sasaki, and K. Yokota, Makromol. Chem., 189, 1279 (1988).
T. Kakuchi, T. Takaoka, and K. Yokota, Makromol. Chem., 189, 2007 (1988).
T. Kakuchi, T. Hasegawa, H. Sasaki, H. Ohmori, K. Yamaguchi, and K. Yokota, Makromol. Chem., 190, 2091 (1989).
T. Kakuchi, T. Takaoka, and K. Yokota, Makromol. Chem., 190, 2449 (1989).
T. Kakuchi, O. Kobayashi, D. Nakaya, and K. Yokota, Polym. J., 21, 649 (1989).
D. S. Lingenfelter, R. C. Helgeson, and D. J. Cram, J. Org. Chem., 46, 393 (1981).
M. Newcomb, J. L. Toner, R. C. Helgeson, and D. J. Cram, J. Am. Chem. Soc., 101, 4941 (1979).
T. Yamaguchi, T. Shimbo, K. Nishimura, and M. Sugiura, Maku (Membrane), 10, 178 (1985).
G. D. Y. Sogah and D. J. Cram, J. Am. Chem. Soc., 101, 3035 (1979).
L. R. Sausa, G. D. Y. Sogah, D. H. Hoffman, and D. J. Cram, J. Am. Chem. Soc., 100, 4569 (1978).
T. Shimbo, T. Yamaguchi, K. Nishimura, and M. Sugiura, J. Chromatogr., 405, 145 (1987).
N. Ashikari and A. Nishimura, J. Polym. Sci., 31, 250 (1958).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kakuchi, T., Takaoka, T. & Yokota, K. Polymeric Chiral Crown Ethers VI. Optical Resolution of α-Amino Acid by Polymers Incorporating 1,3;4,6-Di-O-benzylidene-D-mannitol Residues. Polym J 22, 199–205 (1990). https://doi.org/10.1295/polymj.22.199
Issue Date:
DOI: https://doi.org/10.1295/polymj.22.199
Keywords
This article is cited by
-
Methods for separation of organic and pharmaceutical compounds by different polymer materials
Korean Journal of Chemical Engineering (2014)
-
Enantioseparation using apoenzymes immobilized in a porous polymeric membrane
Nature (1997)
-
Synthesis of poly(dibenzo-19-crown-6) via cyclopolymerization of diepoxide
Polymer Bulletin (1991)