Reactive & Functional Polymers, Vol.37, No.1, 293-298, 1998
Enantioselective permeability of membranes prepared from polyacrylonitrile-graft-(1 -> 6)-2,5-anhydro-D-glucitol
Enantioselective permeation of racemic amino acid perchlorates has been studied using a solid membrane prepared from polyacrylonitrile-graft-(1 --> 6)-2,5-anhydro-3,4-di-O-methyl-D-glucitol. The permeation rates of the amino acids decreased in the order of phenylglycine > phenylalanine > tryptophane, according to the molecular size of the guest compounds. For all the amino acids tested, the permeation rate of the D-isomer was greater than that of the L-isomer. When D- and L-phenylglycine perchlorates were permeated, the D-isomer permeated 1.17 times faster than the L-isomer. During transport using racemic phenylglycine perchlorate, the D-isomer was permeated first and the optical purity was 75% ee (max.). For the adsorption experiment for racemic phenylglycine, the L-isomer was more strongly adsorbed than the D-isomer (5.8% ee). From these data, it was directly made clear that the (1 --> 6)-2,5-anhydro-3,4-di-O-methyl-D-glucitol moieties in the membrane preferentially interacted with the L-isomer rather than with the D-isomer.
Keywords:RACEMIC AMINO-ACID;OPTICAL RESOLUTION;ION;CYCLOPOLYMERIZATION;PERMEATION;TRANSPORT;IONOPHORE;MONENSIN;METAL;ESTER