Chiral polyamides consisting of N‐α‐benzoyl‐L‐glutamic acid as a diacid component

Abstract

AbstractNovel polyamide with chiral environment was obtained from aromatic diamine, 4,4′‐diaminodiphenylmethane (DADPM), and N‐α‐protected L‐glutamic acid, N‐α‐benzoyl‐L‐glutamic acid (Benzoyl‐L‐Glu‐OH). The optical rotation ([α]D) of the polyamide was determined to be 3.6° (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. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 2530–2538, 2009