CUPRIC ION CHELATION ASSISTED SYNTHESIS OF N(ALPHA)-PROTECTED N(OMEGA)-ACRIDIN-9-YL ALPHA,OMEGA-DIAMINO CARBOXYLIC-ACIDS

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