Synthesis of a-L-fucopyranoside-presenting glycoclusters and
investigation of their interaction with recombinant
Photorhabdus asymbiotica lectin (PHL)

J 2018

Synthesis of a-L-fucopyranoside-presenting glycoclusters and investigation of their interaction with recombinant Photorhabdus asymbiotica lectin (PHL)

JANČAŘÍKOVÁ, Gita, Mihály HERCZEG, Eva FUJDIAROVÁ, Josef HOUSER, Katalin E. KÖVÉR et. al.

Základní údaje

Originální název

Synthesis of a-L-fucopyranoside-presenting glycoclusters and investigation of their interaction with recombinant Photorhabdus asymbiotica lectin (PHL)

Autoři

JANČAŘÍKOVÁ, Gita (203 Česká republika, domácí), Mihály HERCZEG (348 Maďarsko), Eva FUJDIAROVÁ (203 Česká republika, domácí), Josef HOUSER (203 Česká republika, domácí), Katalin E. KÖVÉR (348 Maďarsko), Anikó BORBÁS (348 Maďarsko), Michaela WIMMEROVÁ (203 Česká republika, garant, domácí) a Magdolna CSÁVÁS (348 Maďarsko)

Vydání

Chemistry - A European Journal, VCH, 2018, 0947-6539

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10600 1.6 Biological sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.160

Kód RIV

RIV/00216224:14740/18:00102210

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/chem.201705853

UT WoS

000427563000023

Klíčová slova anglicky

fucoclusters; lectin; multivalency; Photorhabdus asymbiotica; agglutination

Štítky

CF BIC, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 28. 3. 2019 14:16, prof. RNDr. Michaela Wimmerová, Ph.D.

Anotace

V originále

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.

Návaznosti

CZ.02.1.01/0.0/0.0/16_013/0001776, interní kód MU
(Kód CEP: EF16_013/0001776)

Název: CIISB - Česká infrastruktura pro integrativní strukturní biologii pro lidské zdraví (Akronym: CIISB4HEALTH)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CIISB - Česká infrastruktura pro integrativní strukturní biologii pro lidské zdraví, PO 1 Posilování kapacit pro kvalitní výzkum

LM2015043, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

LTC17076, projekt VaV

Název: Interdisciplinární přístup ke studiu biologických systémů na molekulární úrovni

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Interdisciplinární přístup ke studiu biologických systémů na molekulární úrovni, INTER-COST

Citovat

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). 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.

@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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