Deoxyfluorination as a Promising Synthetic Approach to Selective Carbohydrate-based Galectin Inhibitors.

0550045 - ÚCHP 2022 CZ eng A - Abstract
Kurfiřt, Martin - Dračínský, Martin - Bojarová, Pavla - Karban, Jindřich
Deoxyfluorination as a Promising Synthetic Approach to Selective Carbohydrate-based Galectin Inhibitors.
Czech Chemial Society Symposium Series, Vol 19, No 1. Praha: Česká společnost chemická, 2021 - (Řápková, R.; Fusek, M.; Drašar, P.). s. 22-23. ISSN 2336-7202.
[Interdisciplinary Meeting of Young Biologists, Biochemists and Chemists /20./ on-line meeting. 17.05.2021-20.05.2021]
R&D Projects: GA MŠMT(CZ) LTC20052
Institutional support: RVO:67985858 ; RVO:61388963 ; RVO:61388971
Keywords : galectins * fluorinated carbohydrates * glycosylation
OECD category: Organic chemistry; Organic chemistry (MBU-M); Organic chemistry (UOCHB-X)

In this work, a complete series of mono-deoxyfluorinated N-acetyllactosamine analogues (6 compounds) have been prepared. The synthesis of each analogue required about 15 synthetic steps, including stereoselective deoxyfluorination of monosaccharide precursors and chemical glycosylation. The binding affinities of the prepared analogues to human gal-1 and gal-3 were determined by ELISA assay and 19F NMR T2-filter techniques. These experiments revealed that individual galectins tolerate fluorine at different positions which makes deoxyfluorinated carbohydrates promising galectin inhibitors.
Permanent Link: http://hdl.handle.net/11104/0325898