Model Studies on Flavin-Dependent Carbonyl-Activation: Reduction of Carbonyl Compounds by Flavohydroquinone

Abstract

The reduction of aldehydes by flavohydroquinone to yield the corresponding alcohols and flavoquinone is reported and discussed in view of its relevance to the mechanism of flavin-dependent dehydrogenation and carbonyl activation. With formaldehyde and flavohydroquinone formation of a covalent 5- (HO - CH₂) Fl_red⁻ intermediate species is observed. In a reverse reaction 5-methylflavoquinonium cation undergoes an internal redox reaction to yield flavohydroquinone and formaldehyde.