Menaquinone-2 and ubiquinone-2 adopt folded, U-shaped conformations contradicting current dogma
Date
2017
Authors
Koehn, Jordan T., author
Crick, Dean C., author
Crans, Debbie C., author
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Abstract
The conformations of long polymers of isoprene units such as those found in the side-chains of lipoquinones involved in bacterial (i.e. Mycobacterium tuberculosis) and eukaryotic electron transport systems (ETS) have not been characterized. First, menaquinone-2 and ubiquinone-2 were synthesized then using 1H-1H 2D NOESY and ROESY NMR spectroscopy, we demonstrated that both molecules adopt a folded, U-shaped conformation in solution and within a model membrane interface. These folded conformations are in stark contrast to the extended conformations seen in literature. Folded conformations likely affect reactivity, function, and recognition within the ETS and provide insight into drug development of potent inhibitors.
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Subject
menaquinone
NMR spectroscopy
ubiquinone
folded conformation
model membrane system