In this paper structure and electronic properties of luteolin and apigenin and all their possible anionic species have been
investigated with DFT and MP2 methods. Molecular geometries have been optimized obtaining for all systems non-planar structures
except for the deprotonated species in 4’ position. Potential energy proles as a function of the torsional angle between B
phenyl ring and 1,4-benzopyrone have been computed for luteolin and apigenin and their corresponding anionic species in 4’
position. Electronic structure for both neutral avonoids has been analyzed with DFT(B3LYP) investigating the frontier molecular
orbitals in terms of energy and character. Finally, changes on the electronical structure upon deprotonation have been evaluated.
[Show abstract][Hide abstract] ABSTRACT: Flavonoids constitute an important class of bioactive molecules, the physicochemical properties of which can be modulated by glucosylation. A structurally guided approach has been used to isolate glucansucrases modified in their acceptor-binding site and specialized for luteolin glucosylation. Of a small-size library, we isolate mutants showing up to an 8-fold increase in flavonoid conversion rate over that observed with the parental enzyme. Di- and triglucosylated luteolin derivatives never described before have been obtained. They exhibit 282- and 17 708-fold increases in water solubility, respectively, and are protected from oxidation by the glucosylation reaction. Molecular docking enables insight into the product specificity of the best mutants. These results demonstrate that α-transglucosylase engineering is a powerful means to generate highly specific catalysts for flavonoid glucosylation and deliver new structural scaffolds with increased bioavailability and high relevance for therapeutic applications.
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