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Synthesis and unexpected binding of monofluorinated N,Nʹ-diacetylchitobiose and LacdiNAc to wheat germ agglutinin.
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SYSNO ASEP 0585671 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis and unexpected binding of monofluorinated N,Nʹ-diacetylchitobiose and LacdiNAc to wheat germ agglutinin. Author(s) Kurfiřt, Martin (UCHP-M) RID, ORCID, SAI
Hamala, Vojtěch (UCHP-M) RID, SAI, ORCID
Beránek, J. (CZ)
Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Červený, Jakub (MBU-M) ORCID, RID
Dračínský, Martin (UOCHB-X) RID, ORCID
Bernášková, Jana (UCHP-M) RID, SAI
Spiwok, V. (CZ)
Bosáková, Z. (CZ)
Bojarová, Pavla (MBU-M) ORCID
Karban, Jindřich (UCHP-M) RID, ORCID, SAIArticle number 107395 Source Title Bioorganic Chemistry. - : Elsevier - ISSN 0045-2068
Roč. 147, June 2024 (2024)Number of pages 12 s. Language eng - English Country NL - Netherlands Keywords fluorinated carbohydrates ; chemical synthesis ; wheat germ agglutinin ; ELLA OECD category Organic chemistry R&D Projects GA23-05146S GA ČR - Czech Science Foundation (CSF) LTC20052 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) LM2023055 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Research Infrastructure e-INFRA CZ II - 90254 - CESNET, zájmové sdružení právnických osob Method of publishing Limited access Institutional support UCHP-M - RVO:67985858 ; MBU-M - RVO:61388971 ; UOCHB-X - RVO:61388963 UT WOS 001238378800001 EID SCOPUS 85192074801 DOI https://doi.org/10.1016/j.bioorg.2024.107395 Annotation Fluorination of carbohydrate ligands of lectins is a useful approach to examine their binding profile, improve their metabolic stability and lipophilicity, and convert them into 19F NMR-active probes. However, monofluorination of monovalent carbohydrate ligands often leads to a decreased or completely lost affinity. By chemical glycosylation, we synthesized the full series of methyl β-glycosides of N,N′-diacetylchitobiose (GlcNAcβ (1–4)GlcNAcβ1-OMe) and LacdiNAc (GalNAcβ(1–4)GlcNAcβ1-OMe) systematically monofluorinated at all hydroxyl positions. A competitive enzyme-linked lectin assay revealed that the fluorination at the 6′-position of chitobioside resulted in an unprecedented increase in affinity to wheat germ agglutinin (WGA) by one order of
magnitude. For the first time, we have characterized the binding profile of a previously underexplored WGA ligand LacdiNAc. Surprisingly, 4′-fluoro-LacdiNAc bound WGA even stronger than unmodified LacdiNAc. These observations were interpreted using molecular dynamic calculations along with STD and transferred NOESY NMR techniques, which gave evidence for the strengthening of CH/π interactions after deoxyfluorination of the
side chain of the non-reducing GlcNAc. These results highlight the potential of fluorinated glycomimetics as highaffinity ligands of lectins and 19F NMR-active probe.Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2025 Electronic address https://hdl.handle.net/11104/0353359
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