Modelling flavoenzymatic charge transfer events: development of catalytic indole deuteration strategies

Abstract

The formation and chemistry of flavin–indole charge transfer (CT) complexes has been studied using a model cationic flavin. The ability to form a CT complex is sensitive to indole structure as gauged by spectroscopic, kinetics and crystallographic studies. Single crystals of sufficient quality of a flavin–indole CT complex, suitable for X-ray diffraction, have been grown, allowing solid-state structural analysis. When CT complex formation is conducted in d₄-methanol, an efficient and synthetically useful C-3 indole deuteration is observed.