Conformation and hydrogen bonding in fluorinated oligosaccharides

Important aspects in the design of carbohydrate-based therapeutics and materials are their conformational properties, which are partly determined by intramolecular hydrogen bonds (H-bonds). To achieve the desired properties of these compound classes, regio- and stereoselective introduction of fluorine is used. However, the influence of fluorine on the intramolecular H-bonds in oligosaccharides formed by functional groups vicinal to fluorine has not been investigated. The aim of this project is to investigate this influence and to elucidate the conformation of selected fluorinated oligosaccharides. Fluorinated disaccharides derived from N-acetyllactosamine and fluorinated trisaccharides derived from the Lewis X antigen (Lewis^X) will be synthesized and used to study inter-residue H-bonds including the non-conventional H-bond, which stabilizes Lewis^X. A combination of computational approaches and NMR experiments will be used to elucidate the conformational states and to detect and evaluate intramolecular H-bonds.

Reference:         Kurfiřt, M. et al. J. Org. Chem. 2024, 89, 11875. DOI: 10.1021/acs.joc.4c00879.

Required education and skills

• Master degree in chemistry.
• The willingness to learn and apply advanced methods of organic synthesis and structure elucidation.