ANTIMETABOLITES PRODUCED BY MICROORGANISMS. VI 1) L-N5-(1-IMINOETHYL) ORNITHINE

A new antimetabolite of arginine and metabolically related compounds was isolated from a fermentation broth produced by an unclassified Streptomycete. The structure was shown to be L-N5-(1-iminoethyl) ornithine and the compound was synthesized by reaction of the copper complex of L-ornithine with ethyl acetimidate. Mild base hydrolysis of the compound gave the expected products, L-ornithine and L-N5-acetylornithine and, in addition, a rearranged product, L-N2-acetylornithine. Arginase hydrolyzed the antimetabolite to L-ornithine.