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Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside.

ABSTRACT: A series of alkyl thioglycosides and alkyl thiodiglycosides bearing glucose and N-acetylglucosamine residues were prepared by thiol-ene coupling in moderate to good yields (40-85%). Their binding ability towards wheat germ agglutinin was measured by competitive enzyme-linked lectin assays. One of the synthetic compounds presenting two GlcNAc units showed the highest inhibitory effect of this study with an IC₅₀ of 11 µM corresponding to a 3182-fold improvement compared to GlcNAc. These synthetic molecules were used to produce giant vesicles, alone or in mixture with phospholipids, mimicking bacterial outer membrane vesicles (OMV) with potential antiadhesive properties.

SUBMITTER: Fayolle D

PROVIDER: S-EPMC6541351 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside.

Fayolle Dimitri D Berthet Nathalie N Doumeche Bastien B Renaudet Olivier O Strazewski Peter P Fiore Michele M

Beilstein journal of organic chemistry 20190417

A series of alkyl thioglycosides and alkyl thiodiglycosides bearing glucose and <i>N</i>-acetylglucosamine residues were prepared by thiol-ene coupling in moderate to good yields (40-85%). Their binding ability towards wheat germ agglutinin was measured by competitive enzyme-linked lectin assays. One of the synthetic compounds presenting two GlcNAc units showed the highest inhibitory effect of this study with an IC<sub>50</sub> of 11 µM corresponding to a 3182-fold improvement compared to GlcNAc ...[more]

PMID: 31164930

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2008-10-03 | GSE11047 | GEO

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