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Issue 15, 2016
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Modelling flavoenzymatic charge transfer events: development of catalytic indole deuteration strategies

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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.

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

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Article information


Submitted
15 Feb 2016
Accepted
15 Mar 2016
First published
15 Mar 2016

Org. Biomol. Chem., 2016,14, 3787-3792
Article type
Paper
Author version available

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

A. T. Murray, J. D. Challinor, C. E. Gulácsy, C. Lujan, L. E. Hatcher, C. R. Pudney, P. R. Raithby, M. P. John and D. R. Carbery, Org. Biomol. Chem., 2016, 14, 3787
DOI: 10.1039/C6OB00361C

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