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@article{1404164,
author = {Jančaříková, Gita and Herczeg, Mihály and Fujdiarová, Eva and Houser, Josef and Kövér, Katalin E. and Borbás, Anikó and Wimmerová, Michaela and Csávás, Magdolna},
article_number = {16},
doi = {http://dx.doi.org/10.1002/chem.201705853},
keywords = {fucoclusters; lectin; multivalency; Photorhabdus asymbiotica; agglutination},
language = {eng},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
title = {Synthesis of a-L-fucopyranoside-presenting glycoclusters and investigation of their interaction with recombinant Photorhabdus asymbiotica lectin (PHL)},
url = {http://onlinelibrary.wiley.com/doi/10.1002/chem.201705853/full},
volume = {24},
year = {2018}
}
TY - JOUR
ID - 1404164
AU - Jančaříková, Gita - Herczeg, Mihály - Fujdiarová, Eva - Houser, Josef - Kövér, Katalin E. - Borbás, Anikó - Wimmerová, Michaela - Csávás, Magdolna
PY - 2018
TI - Synthesis of a-L-fucopyranoside-presenting glycoclusters and investigation of their interaction with recombinant Photorhabdus asymbiotica lectin (PHL)
JF - Chemistry - A European Journal
VL - 24
IS - 16
SP - 4055-4068
EP - 4055-4068
PB - VCH
SN - 09476539
KW - fucoclusters
KW - lectin
KW - multivalency
KW - Photorhabdus asymbiotica
KW - agglutination
UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201705853/full
N2 - Photorhabdus asymbiotica is a gram-negative bacterium that is not only as effective an insect pathogen as other members of the genus, but it also causes serious diseases in humans. The recently identified lectin PHL from P. asymbiotica verifiably modulates an immune response of humans and insects, which supports the idea that the lectin might play an important role in the host-pathogen interaction. Dimeric PHL contains up to seven L- fucose specific binding sites per monomer, and in order to target multiple binding sites of PHL, a-L-fucoside-containing di-, tri- and tetravalent glycoclusters were synthesized. Methyl gallate and pentaerythritol were chosen as multivalent scaffolds, and the fucoclusters were built from the above-mentioned cores by coupling with different oligoethylene bridges and propargyl a-L-fucosides using 1,3-dipolar azide-alkyne cycloaddition. The interaction between fucoside derivates and PHL was investigated by several biophysical and biological methods, ITC and SPR measurements, hemagglutination inhibition assay and an investigation of bacterial aggregation properties were carried out. Moreover, details of the interaction between PHL and propargyl a-L-fucoside as a monomer unit were revealed using X-ray crystallography. Besides this, the interaction with multivalent compounds was studied by NMR techniques. The newly synthesized multivalent fucoclusters proved to be up to several orders of magnitude better ligands than the natural ligand, L-fucose.
ER -
JANČAŘÍKOVÁ, Gita, Mihály HERCZEG, Eva FUJDIAROVÁ, Josef HOUSER, Katalin E. KÖVÉR, Anikó BORBÁS, Michaela WIMMEROVÁ a Magdolna CSÁVÁS. Synthesis of a-L-fucopyranoside-presenting glycoclusters and investigation of their interaction with recombinant Photorhabdus asymbiotica lectin (PHL). \textit{Chemistry - A European Journal}. VCH, 2018, roč.~24, č.~16, s.~4055-4068. ISSN~0947-6539. Dostupné z: https://dx.doi.org/10.1002/chem.201705853.
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