A convenient method to synthesize phosphinic peptides containing an aspartyl or glutamyl aminophosphinic acid. Use of the phenyl group as the carboxyl synthon

Article abstract of DOI:10.1016/S0040-4020(99)00910-2

Many attempts to synthesize AspΨ(PO₂CH₂)Ala phosphinic pseudodipeptides by Michael addition of aspartyl aminophosphinic acid to ethyl methacrylate have failed. The preparation of such phosphinic peptides was finally achieved starting from a protected PheΨ(PO₂CH₂)Ala phosphinic building block. The key step is a mild oxidation of the phenyl group to carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.