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

Abstract

The synthesis of N^α-protected N^ω-acridin-9-yl derivatives of the α,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 α-amino and carboxy groups. N^α-Fmoc protection was introduced by using N-(fluoren-9-ylmethoxycarbonyloxy)succinimide in aqueous dioxan.