Journal of Polymer Science Part A: Polymer Chemistry, Vol.47, No.10, 2530-2538, 2009
Chiral Polyamides Consisting of N-alpha-Benzoyl-L-Glutamic Acid as a Diacid Component
Novel polyamide with chiral environment was obtained from aromatic diamine, 4,4'-diaminodipbenyl methane (DADPM), and N-alpha-protected L-glutamic acid, N-alpha-benzoyl-L-glutamic acid (Benzoyl-L-Glu-OH). The optical rotation ([alpha](D)) of the polyamide was determined to be 3.6 degrees (c =1.00 g/dL in DMF), implying that the optically active polyamide was obtained. The present polyamide gave a durable self-standing membrane. The membrane selectively incorporated the D-isomer of Ac-Trp from racemic mixture of Ac-Trp. The adsorption selectivity toward Ac-D-Trp was determined to be 1.95. It showed chiral separation ability by adopting potential difference as a driving force for membrane transport. The permselectivity was dependent on the potential difference, and at the applied potential difference of 3.0 V, the membrane selectively transported Ac-D-Trp and the permselectivity toward Ac-D-Trp was determined to be 1.84, which was close to the adsorption selectivity of 1.95. Contrary to this, the membrane showed opposite permselectivity at the applied potential difference of 2.0 V and the permselectivity toward the L-isomer reached 2.48. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2530-2538, 2009
Keywords:adsorption selectivity;chiral polyamides;chiral separation;electrodialysis;membranes;optical resolution;permselectivity;polyamides