Cupric Ion Chelation Assisted Synthesis of N(α)-Protected N(ω)-Acridin-9-yl α,ω-Diamino Carboxylic Acids

Abstract

The synthesis of Na-protected N?-acridin-9-yl derivatives of the a,w-diamino carboxylic acids ornithine and lysine is reported. Direct introduction of the acridin-9-yl moiety to the amino side chain of the free amino acid was achieved in methanol through temporary copper(II) chelation protection of the a-amino and carboxy groups. Na-Fmoc protection was introduced by using N-(fluoren-9-ylmethoxycarbonyloxy)succinimide in aqueous dioxan.