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

Alexander T Murray; Jonathan D Challinor; Christina E Gulácsy; Cristina Lujan; Lauren E Hatcher; Christopher R Pudney; Paul R Raithby; Matthew P John; David R Carbery

doi:10.1039/c6ob00361c

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

Alexander T Murray, Jonathan D Challinor, Christina E Gulácsy, Cristina Lujan, Lauren E Hatcher, Christopher R Pudney, Paul R Raithby, Matthew P John, David R Carbery

GlaxoSmithKline

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8 Citations (SciVal)

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.

Original language	English
Pages (from-to)	3787-3792
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	15
Early online date	23 Mar 2016
DOIs	https://doi.org/10.1039/c6ob00361c
Publication status	Published - 21 Apr 2016

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10.1039/c6ob00361c

http://dx.doi.org/10.1039/c6ob00361c

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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.",

author = "Murray, {Alexander T} and Challinor, {Jonathan D} and Gul{\'a}csy, {Christina E} and Cristina Lujan and Hatcher, {Lauren E} and Pudney, {Christopher R} and Raithby, {Paul R} and John, {Matthew P} and Carbery, {David R}",

year = "2016",

month = apr,

day = "21",

doi = "10.1039/c6ob00361c",

language = "English",

volume = "14",

pages = "3787--3792",

journal = "Organic and Biomolecular Chemistry",

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TY - JOUR

T1 - Modelling flavoenzymatic charge transfer events

T2 - development of catalytic indole deuteration strategies

AU - Murray, Alexander T

AU - Challinor, Jonathan D

AU - Gulácsy, Christina E

AU - Lujan, Cristina

AU - Hatcher, Lauren E

AU - Pudney, Christopher R

AU - Raithby, Paul R

AU - John, Matthew P

AU - Carbery, David R

PY - 2016/4/21

Y1 - 2016/4/21

N2 - 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.

AB - 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.

UR - http://dx.doi.org/10.1039/c6ob00361c

U2 - 10.1039/c6ob00361c

DO - 10.1039/c6ob00361c

M3 - Article

C2 - 27005963

SN - 1477-0520

VL - 14

SP - 3787

EP - 3792

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 15

ER -

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

Abstract

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RCaH Impact Acceleration Fellowships and Workshops

Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

Modular Helicenoid Lewis Base Catalysts Applied to Modern Synthesis and Materials

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this

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

Abstract

Access to Document

Other files and links

Fingerprint

Projects

RCaH Impact Acceleration Fellowships and Workshops

Applying Long-Lived Metastable States in Switchable Functionality via Kinetic Control of Molecular Assembly

Modular Helicenoid Lewis Base Catalysts Applied to Modern Synthesis and Materials

Equipment

MC2- Nuclear Magnetic Resonance (NMR)

MC2- X-ray diffraction (XRD)

Cite this