Synthesis of substituted imidazoles and dimerization products using cells and laccase from Trametes versicolor

Feeding N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides to cells of Trametes versicolor yielded two types of aromatic metabolites besides degradation products: (1) Novel heteroaromatic compounds, such as: N-[5-formyl-4-phenyl-2-(propylamino)imidazol-1-yl]-acetamide, 4-phenyl-2-(propylamino)imidazole, N-(3-hydroxy-4-phenyl-2-propylimino-2,3-dihydroimidazol-1-yl)-acetamide, and N-(5-oxo-4-phenyl-2-propylimino-2,5-dihydroimidazol-1-yl)-acetamide; (2) Novel compounds arising from coupling of two ring-opened molecules of the substrate.