Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

• Leon M. Friedrich and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

• glycophotoswitches in their different isomeric states led to new insights into the role of ligand orientation in carbohydrate recognition. The experimental results were underpinned by molecular modeling. Keywords: azobenzene glycoconjugates; carbohydrate recognition; docking; FimH; orthogonal photoswitching

• hypothesize that isomerization of the azo group in the tested azobenzene glycoconjugates controls the orientation of the attached glycoligand and therefore, different glycoazobenzene isomers show various affinities for the bacterial lectin FimH as reflected by the measured RIP values. This is clearly seen

• azobenzene glycoconjugates 1–5 in complex with the bacterial lectin FimH. Molecular modeling Docking studies were performed with the different isomers (E and Z or EE, EZ, ZE, and ZZ) of the azobenzene glycoconjugates 1, 2, 4, and 5, containing a mannoside ligand, and the bacterial lectin FimH (for 3, cf