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Regioselective Arene Halogenation using the FAD-Dependent Halogenase RebH


  • This work was supported by an NIH Pathways to Independence Award (5R00GM087551) and a Searle Scholar Award (11-SSP-202) to J.C.L., an NIH Chemistry and Biology Interface training grant to J.T.P. (T32 GM008720), and an NSF predoctoral fellowship to M.C.A. (DGE-1144082). We thank Prof. Karl-Heinz van Pée and Dr. Eugenio P. Patallo for helpful discussions, Prof. Chris T. Walsh for donating plasmids encoding RebH and RebF, and Prof. Stephen Bottomley for a plasmid encoding MBP.


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Together we're strong: Co-expression of the halogenase RebH with GroEL/ES and fusion of the flavin reductase RebF to MBP enabled production of both enzymes on scales sufficient for preparative regioselective oxidative halogenation of arenes. The activity and selectivity of RebH contrasts with those reported for the structurally homologous halogenase PrnA, which only enabled halogenation of nonnatural substrates at their most electronically activated positions.