Comparison of Conformational Analyses of Naturally Occurring Flavonoid-O-Glycosides with Unnatural Flavonoid-CF₂-Glycosides Using Molecular Modeling.

ABSTRACT: Many glycosylated natural products display biological activity and are deglycosylated by the metabolic processes of the body. Although unnatural CF₂-glycosides have been proposed as nonhydrolyzable analogues, CF₂-derivatives of natural products are exceedingly challenging to synthesize and few examples exist. These difluorinated molecules may have unique conformational behavior as a consequence of changing the glycosidic linkage. In this study, we performed conformational searches using MacroModel followed by molecular dynamics simulations to investigate the conformational behavior of the glycosidic bonds in flavonoid-O-glycosides and in corresponding CF₂-glycosylated derivatives. Compared to their O-glycosylated analogues, flavonoid-3-CF

SUBMITTER: Alkhodier RA 

PROVIDER: S-EPMC9904208 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature