Studies on the biosynthesis of violacein. part I Biosynthesis of violacein : A novel rearrangement in tryptophan metabolism with a 1,2-shift of the indole ring.

Abstract

A number of studies have been reported on the blue pigment, violacein, and its producing bacterium, Chromobdcteriumviolaceum, since its discovery in 1882.1} Violacein possesses antibiotic activities against various microorganisms.2) Its chemical structure was proposed by a series of degradation studies, and was ascertained by chemical synthesis in 1958.3)" The structure consists of three units, i.e., the 5-hydroxyindole, oxindole and 2-pyrrolidone moieties. Someinvestigations on the biosynthesis of vialacein have appeared; by tracer experiments with various 14C-labeled compounds, it has been demonstrated that l-8 V* r=oh,violacein r=h, deoxyviolacein