Deoxyfluorinated N-acetyllactosamines as Tailored Carbohydrate-based Probes for Human Galectins.

0543682 - ÚCHP 2022 CZ eng K - Conference Paper (Czech conference)
Kurfiřt, Martin
Deoxyfluorinated N-acetyllactosamines as Tailored Carbohydrate-based Probes for Human Galectins.
Proceedings of Abstracts. Prague: Institute of Chemical Process Fundamentals of the CAS, v. v. i., 2021 - (Bendová, M.; Wagner, Z.), s. 16-17. ISBN 978-80-86186-41-2.
[Bažant Postgraduate Conference 2021. Prague (CZ), 23.06.2021-26.06.2021]
R&D Projects: GA MŠMT(CZ) LTC20052; GA MŠMT(CZ) LTC20072
Grant - others:MEYS(XE) CA18103
Institutional support: RVO:67985858
Keywords : NMR techniques * deoxyfluorinated N-acetyllactosamines * human alectins
OECD category: Organic chemistry

this work, I prepared a complete series of mono‑deoxyfluorinated N-acetyllactosamine analogues 1-6. The synthesis of each analogue
required approximately 15 synthetic steps, including deoxyfluorination of monosaccharide precursors, chemical glycosylation and
deprotection. Their binding affinities to the two most explored human galectin-1 and -3 were determined by ELISA and 19F NMR T2-filter
techniques, which enabled the identification of hydroxyl groups, crucial in the non-covalent recognition by galectins. This binding study
also permitted to compare both tested galectins in terms of their substrate specificity, revealing subtle differences, which could be utilized
in the development of selective galectin inhibitors. Furthermore, the series is also a perfect tool to study the molecular origin of recognition
events via epitope-mapping 19F NMR techniques.
Permanent Link: http://hdl.handle.net/11104/0320862