Synthesis of polyamide containing optically active thymine derivative as a grafted pendant

Abstract

A new route to polyamides containing optically active thymine groups as pendants has been established. The method is based on the grafting of (–) and (±)-2-(thymin-1-yl)propionic acid [(–) and (±) TPA] onto a polyamide containing hydroxyl groups. The hydroxy polyamide was prepared by selective N -acylation of an active diester of N -hydroxy-5-norborene-2,3-dicarboxamide (HONB), N , N '-(isophthaloyl-dioxy)-bis(5-norbornene-2,3-dicarboximide) (IPBONB), with 1,3-diamino-2-hydroxypropane (AHP). Model compounds (−) and (±)-(1,3-dibenzoylamino-2-propyl)2-(thymin-1-yl)propionate[(−) and (±) (BAPTP)] were prepared by direct, low-temperature esterification before synthesizing the polymer.