Synthesis of l -Epicapreomycidine

Abstract

A cyclic guanidino amino acid, l-epicapreomycidine, isolated from hydrolyzates of protease inhibitors such as chymostatin and elastatinal was synthesized. This amino acid is a diastereomer of l-capreomycidine which is a component amino acid of tuberactinomycin N,O and capreomycin. A new synthetic route from β-hydroxy-Dl-orni thine via an aziridine compound to Dl-capreomycidine was applied to the synthesis of l-epicapreomycidine starting from erythro-β-hydroxy-l-ornithine. A convenient and one-step technique to obtain l-erythro form from a mixture of four diastereomers of β-hydroxyornithine by means of enzymatic reaction was newly exploited. The synthetic l-epicapreomycidine obtained was identical with natural one in all respects, thus confirming the proposed structure.