Issue 37, 2020

Catechol-functionalized sequence-defined glycomacromolecules as covalent inhibitors of bacterial adhesion

Abstract

Herein, we present the synthesis of catechol functionalized sequence-defined glycomacromolecules that can covalently block the binding site of lectins and bacterial adhesins. These structures produced on a solid phase support combine two important features: the multivalent presentation of carbohydrates for specificity, and catechols as anchors to go from highly reversible interactions to covalent attachment and more efficient inhibition. In our study we demonstrate this on the lectin Concanavalin A (ConA) by showing an increase in clustering for catechol ligands and on the effective inhibition of bacterial adhesion of E. coli on mannan surfaces by our catechol functionalized glycomacromolecules. Furthermore, covalent attachment is studied via MALDI-TOF measurements and SDS-PAGE analysis. Importantly, by replacing binding sugars with non-binding sugars, no inhibitory effects or covalent attachment were observed.

Graphical abstract: Catechol-functionalized sequence-defined glycomacromolecules as covalent inhibitors of bacterial adhesion

Supplementary files

Article information

Article type
Paper
Submitted
07 iyl 2020
Accepted
19 avq 2020
First published
26 avq 2020

Polym. Chem., 2020,11, 6091-6096

Catechol-functionalized sequence-defined glycomacromolecules as covalent inhibitors of bacterial adhesion

L. Fischer, R. C. Steffens, T. J. Paul and L. Hartmann, Polym. Chem., 2020, 11, 6091 DOI: 10.1039/D0PY00975J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements