Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH

• Vijayanand Chandrasekaran,
• Katharina Kolbe,
• Femke Beiroth and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2013, 9, 223–233, doi:10.3762/bjoc.9.26

• adhesive surfaces. Keywords: azobenzene glycosides; bacterial adhesion; E/Z photoisomerisation; FimH antagonists; mannobiosides; molecular switches; sweet switches; Introduction Adhesion of bacteria to surfaces can be a severe problem both in vivo and in vitro. Hence, inhibition of bacterial adhesion by

• studies [8][9][10][11]. It has turned out that the 1,3-linked mannobioside α-D-Man-(1→3)-D-Man (1, Figure 1B) is an ideal disaccharide ligand for FimH [3][12]. All other isomeric mannobiosides do not bind favourably to FimH. Therefore, we have designed the respective azobenzene mannobioside 2 (Figure 1C

• mannobioside 2 was selected as a photoswitchable inhibitor of the bacterial lectin FimH based on earlier findings about the inhibitory potency of several mannobiosides [34][35]. Its synthesis was straightforward and high-yielding. It has very convenient photochromic properties as the E→Z isomerisation is