Biotransformation of N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides and kinetic studies by using cells and laccase from Trametes versicolor.
The product pattern of biotransformation of different N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides were compared. N-(2-alkylamino-4-phenylimidazol-1-yl)-acetamides were transformed by Trametes versicolor into two types of aromatic products identified by chemical structure analysis: 1. Novel heteroaromatic compounds, such as: 2-(alkylamino)-4-phenylimidazoles, N-(2-alkylamino-5-formyl-4-phenylimidazol-1-yl)-acetamides, N-(2-alkylimino-3-hydroxy-4-phenyl-2,3-dihydroimidazol-1-yl)-acetamides and N-(2-alkylimino-5-oxo-4-phenyl-2,5-dihydroimidazol-1-yl)-acetamides, 2. Novel compounds arising from coupling of two molecules of the substrate. These aromatic compounds were produced from the beginning of incubation by cultures of T. versicolor. In addition to these two types of biotransformation products, monoaromatics such as oxophenyl acetic acid, benzoic acid, and benzyl alcohol were formed as degradation products resulting from an extended incubation of the substrates and from the degradation of the first two types of transformation products. Crude preparations of laccase from T. versicolor catalysed only the formation of novel heteroaromatic compounds, though they do so with higher yields and in shorter time than cultures of T. versicolor.
Mikolasch
Annett
A
Institut für Mikrobiologie, Ernst-Moritz-Arndt-Universität, F.-L.-Jahn-Str. 15, 17487 Greifswald, Germany. annett.mikolasch@gmx.de
Schauer
Frieder
F
D000081:Acetamides / Q000737:chemistry* / Q000378:metabolism*; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000032:analysis / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000032:analysis / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry* / Q000378:metabolism*; D007700:Kinetics; D042845:Laccase / Q000302:isolation & purification / Q000378:metabolism*; D020072:Polyporales / Q000201:enzymology / Q000378:metabolism*
D000081:Acetamides; D003470:Culture Media; D006571:Heterocyclic Compounds; D006841:Hydrocarbons, Aromatic; D007093:Imidazoles; D042845:Laccase