Revista Colombiana de Química
versão impressa ISSN 0120-2804
ARISTIZABAL, Diego A.; LEZCANO, Clara S.; GARCIA, Carlos M. e DURANGO, Diego L.. BIOTRANSFORMATION OF 2-PHENYLETHANOL AND ACETOPHENONE BY THE PLANT PATHOGENIC FUNGUS Colletotrichum acutatum. Rev.Colomb.Quim. [online]. 2008, vol.37, n.1, pp. 7-19. ISSN 0120-2804.
The microbial transformation of 2-phenilethanol 1 and acetophenone 2 was investigated using the plant pathogenic fungus Colletotrichum acutatum; the process was carried out in liquid media culture Czapeck-Dox at an average temperature of 24 oC, a relative humidity between 45% and 60% and with agitation in a shaker at 150 rpm. The biotransformation of the substrate 1 produced the metabolic products 1-phenyl-1,2-ethanediol 3, (2- methoxyethyl)benzen 4 and 2-phenylethyl acetate 5, and from substrate 2 were obtained the compounds 1-phenyl- 1,2-ethanediol 3, 1-phenylethanol 6 and 2-phenylethanol 1. The structures of metabolic products were determined by gas chromatography coupled with mass spectrometry (GC-MS) and nuclear magnetic resonance of proton and of carbon (1H and 13C NMR). The process has a strong tendency of the pathogen to produce hydroxylations on the substituents attached to the aromatic ring. Additionally, C. acutatum was effective to reduce the carbonyl group and produce esterification reactions in the hydroxyl groups from primary alcohols. The metabolic pathway of both substrates is discussed.
Palavras-chave : Enzymatic hydroxylations; enzymatic reduction of aromatic ketone; enzymatic esterification of alcohols.