title: 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.
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Alexander T
authors.initials: AT
authors.lastname: Murray
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Challinor
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Christina E
authors.initials: CE
authors.lastname: Gulácsy
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Cristina
authors.initials: C
authors.lastname: Lujan
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Lauren E
authors.initials: LE
authors.lastname: Hatcher
authors.affiliation: Department of Biology and Biochemistry, University of Bath, Bath, BA2 7AY, UK. c.r.pudney@bath.ac.uk.
authors.forename: Christopher R
authors.initials: CR
authors.lastname: Pudney
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: Paul R
authors.initials: PR
authors.lastname: Raithby
authors.affiliation: GlaxoSmithKline Research and Development, Gunnels Wood Road, Stevenage, UK.
authors.forename: Matthew P
authors.initials: MP
authors.lastname: John
authors.affiliation: Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. d.carbery@bath.ac.uk.
authors.forename: David R
authors.initials: DR
authors.lastname: Carbery
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D003903:Deuterium / Q000737:chemistry; D004579:Electron Transport; D038181:FMN Reductase / Q000737:chemistry; D005415:Flavins / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D013302:Streptomyces / Q000201:enzymology
chemical_list: D005415:Flavins; D007211:Indoles; C030374:indole; D003903:Deuterium; D038181:FMN Reductase