BIOTRANSFORMATION OF THE COMPOUNDS 2-PHENYLETHANOL AND ACETOPHENONE BY THE PHYTOPHATOGEN FUNGUS Botryodiplodia theobromae
Keywords:Enzymatic hydroxylations, enzymatic reduction of aromatic ketone, enzymatic esterification
In this study, biotransformations of the substrates 2-phenilethanol 1 and acetophenone 2 achieve by
the phylamentous phytopatogenic fungus Botryodiplodia theobromae, are evaluated; the process is carried out in liquid media culture Czapeck-Dox to an average temperature 24 ºC, relative humidity between 45 % to 60 % and with agitation in shaker 150 rpm. The pathogen is obtained from infected commercial fruits of avocado, acquired at the centers of trade in the city of Medellín (Antioquia-Colombia) and it is characterized morphologically in the Phytopathology Laboratory of the University National Colombia, Medellín. The biotransformation of the substrate 1 produces the metabolites phenylethanodiol 3, 2- phenylacetic acid 4, phenylacetate 2-phenylethyl 5, acetate of 2-phenylethanol 6, and from substrate 2 are obtained the metabolites 1-phenylethanol 7, 2-phenilacetic acid 6, 2-phenylethanol 1, 2-phenylethanal 8, o-hydroxiacetophenone 9 and acetate of 1-phenylethanol 10. The structures of metabolic products are determined by gas chromatography coupled with mass spectrometry (GC-MS) and nuclear magnetic resonance of proton and carbon (1H and 13C NMR). The process is marked by tendency of the pathogen to produce hydroxylations on the alkylic chain and some on the aromatic chain. Additionally, it has the capability to reduce to the carbonyl group and produce esterification reaction in the hydroxyl groups.
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