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Open AccessArticle

Calculation of the Geometries and Infrared Spectra of the Stacked Cofactor Flavin Adenine Dinucleotide (FAD) as the Prerequisite for Studies of Light-Triggered Proton and Electron Transfer

1
CCBG, DETEMA, Facultad de Química, Isidoro de María 1616, 11800 Montevideo, Uruguay
2
Department of Chemistry, Physical and Biophysical Chemistry, Bielefeld University, Universitätsstr. 25, 33615 Bielefeld, Germany
*
Author to whom correspondence should be addressed.
Biomolecules 2020, 10(4), 573; https://doi.org/10.3390/biom10040573
Received: 23 December 2019 / Revised: 25 March 2020 / Accepted: 27 March 2020 / Published: 9 April 2020
Flavin cofactors, like flavin adenine dinucleotide (FAD), are important electron shuttles in living systems. They catalyze a wide range of one- or two-electron redox reactions. Experimental investigations include UV-vis as well as infrared spectroscopy. FAD in aqueous solution exhibits a significantly shorter excited state lifetime than its analog, the flavin mononucleotide. This finding is explained by the presence of a “stacked” FAD conformation, in which isoalloxazine and adenine moieties form a π-complex. Stacking of the isoalloxazine and adenine rings should have an influence on the frequency of the vibrational modes. Density functional theory (DFT) studies of the closed form of FAD in microsolvation (explicit water) were used to reproduce the experimental infrared spectra, substantiating the prevalence of the stacked geometry of FAD in aqueous surroundings. It could be shown that the existence of the closed structure in FAD can be narrowed down to the presence of only a single water molecule between the third hydroxyl group (of the ribityl chain) and the N7 in the adenine ring of FAD. View Full-Text
Keywords: stacked flavin adenine dinucleotide (FAD) in microsolvation; vibrational spectra; supramolecular orbitals stacked flavin adenine dinucleotide (FAD) in microsolvation; vibrational spectra; supramolecular orbitals
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Kieninger, M.; Ventura, O.N.; Kottke, T. Calculation of the Geometries and Infrared Spectra of the Stacked Cofactor Flavin Adenine Dinucleotide (FAD) as the Prerequisite for Studies of Light-Triggered Proton and Electron Transfer. Biomolecules 2020, 10, 573.

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