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

A series of alkyl thioglycosides and alkyl thiodiglycosides bearing glucose and N-acetylglucosamine residues were prepd. 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 compds. 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 mols. were used to produce giant vesicles, alone or in mixt. with phospholipids, mimicking bacterial outer membrane vesicles (OMV) with potential antiadhesive properties.

Références

Titre
Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside.
Type de publication
Article de revue
Année de publication
2019
Revue
Beilstein J. Org. Chem.
Volume
15
Pagination
937–946
ISSN
1860-5397
Soumis le 15 janvier 2020