A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion |
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Authors: | Dr. Guillaume Despras Dr. Leonhard Möckl Dr. Anne Heitmann Insa Stamer Prof. Dr. Christoph Bräuchle Prof. Dr. Thisbe K. Lindhorst |
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Affiliation: | 1. Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3–4, 24118 Kiel, Germany;2. Department of Chemistry and Center for NanoScience (CeNS), University of Munich (LMU), Butenandtstrasse 11, 81377 Munich, Germany;3. Department of Chemistry Education, Leibniz Institute for Science and Mathematics Education, Olshausenstrasse 62, 24118 Kiel, Germany |
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Abstract: | We have recently demonstrated, by employing azobenzene glycosides, that bacterial adhesion to surfaces can be switched through reversible reorientation of the carbohydrate ligands. To investigate this phenomenon further, we have turned here to more complex—that is, multivalent—azobenzene glycoclusters. We report on the synthesis of a photosensitive trivalent cluster mannoside conjugated to an azobenzene hinge at the focal point. Molecular dynamics studies suggested that this cluster mannoside, despite the conformational flexibility of the azobenzene-glycocluster linkage, offers the potential for reversibly changing the glycocluster's orientation on a surface. Next, the photoswitchable glycocluster was attached to human cells, and adhesion assays with type 1 fimbriated Escherichia coli bacteria were performed. They showed marked differences in bacterial adhesion, dependent on the light-induced reorientation of the glycocluster moiety. These results further underline the importance of orientational effects in carbohydrate recognition and likewise the value of photoswitchable glycoconjugates for their study. |
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Keywords: | cell adhesion control of carbohydrate recognition metabolic oligosaccharide engineering multivalency photochemistry |
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