A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand 
Orientation in Bacterial Adhesion

Despras, Guillaume; Möckl, Leonhard; Heitmann, Anne; Stamer, Insa; Braeuchle, Christoph; Lindhorst, Thisbe K.

doi:10.1002/cbic.201900269

アイテム詳細

登録内容を編集ファイル形式で保存

一時保存へ追加

タグ情報を表示リリース履歴を表示詳細要約

公開

学術論文

A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

There are no locators available

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

フルテキスト (公開)

公開されているフルテキストはありません

付随資料 (公開)

There is no public supplementary material available

引用

Despras, G., Möckl, L., Heitmann, A., Stamer, I., Braeuchle, C., & Lindhorst, T. K. (2019). A Photoswitchable Trivalent Cluster Mannoside to Probe the Effects of Ligand Orientation in Bacterial Adhesion. ChemBioChem, 20(18), 2373-2382. doi:10.1002/cbic.201900269.

引用: https://hdl.handle.net/21.11116/0000-0007-678C-8

要旨

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.