Fucosyl glycosides for DC-SIGN targeting: Fucosylation strategies, synthesis and binding studies of model compounds
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F25%3A43931519" target="_blank" >RIV/60461373:22310/25:43931519 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22810/25:43931519
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0968089625001051" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0968089625001051</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.bmc.2025.118164" target="_blank" >10.1016/j.bmc.2025.118164</a>
Alternative languages
Result language
angličtina
Original language name
Fucosyl glycosides for DC-SIGN targeting: Fucosylation strategies, synthesis and binding studies of model compounds
Original language description
DC-SIGN, a C-type lectin receptor expressed on immune cells, is considered a promising target for immunomodulatory and antiviral therapies. While mannose-based glycomimetics have been extensively studied as DC- SIGN ligands, fucose-based strategies remain underexplored. This study explores the fucosylation of linear alcohols and sugars using eight different fucosyl donors, aiming at designing strategies for the development of fucose-based glycomimetics targeting DC-SIGN. Four types of leaving groups and two different acyl-based protecting groups on the donors were tested. The glycosylation of 3-azidopropan-1-ol exclusively yielded the (3-anomer, demonstrating high stereoselectivity. The azido group in the product is versatile, allowing for direct click chemistry reactions or reduction to an amine for further functionalization. Both types of reactions were demonstrated in a model reaction. In the glycosylation of a sugar, a disaccharide moiety of Lewis X antigen was selected as a target molecule. Only one of the eight tested fucosyl donors worked well in this reaction and provided the product in a reasonable yield. The disaccharide was also equipped with the 3-azidopropyl linker, facilitating future modifications. Finally, NMR studies confirmed compatibility of the linker with canonical Ca2+- dependent carbohydrate binding to DC-SIGN, suggesting potential for further development of fucose-based glycomimetics targeting this C-type lectin receptor.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN
0968-0896
e-ISSN
1464-3391
Volume of the periodical
123
Issue of the periodical within the volume
1 June 2025
Country of publishing house
US - UNITED STATES
Number of pages
9
Pages from-to
118164
UT code for WoS article
001457212600001
EID of the result in the Scopus database
2-s2.0-105000988336