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Anaerobic ethylbenzene metabolism

Anaerobic ethylbenzene degradation is initiated by a stereospecific hydroxylation of the hydrocarbon to (S)-1-phenylethanol, catalyzed by the molybdoenzyme ethylbenzene dehydrogenase. We have determined the structure of this enzyme and are currently working on its reaction mechanism by a combination of experimental and computational techniques (in cooperation with M. Szaleniec, Krakow). The enzyme offers a totally novel synthetic path for obtaining chiral alcohols from the corresponding hydrocarbons.

 Fig. 3: left: overall structure of ethylbenzene dehydrogenase, highlighting its metallo-cofactors (from below: Mo-bis-molybdopterin guanine dinucleotide, 5 Fe4S4 clusters, heme b559); right: computer model of enantioselective binding of ethylbenzene in the active sitze of EBDH. © Szaleniec M., Dudzik A., Kozik B.,  Borowski T., Heider J. & Witko M. (2014) Mechanistic basis for the enantioselectivity of anaerobic hydroxylation of alkylaromatic compounds by  ethylbenzene dehydrogenase. J. Inorgan. Biochem. 139, 9-20