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

• DOI: 10.3762/bjoc.9.26
• Publication Date: 2013-02-01T13:15:48Z
• Authors: Vijayanand Chandr...; Katharina Kolbe; Femke Beiroth; Thisbe K Lindhorst
• Keywords: Azobenzene

In order to allow spatial and temporal control of carbohydrate-specific bacterial adhesion, it has become our goal synthesise azobenzene mannosides as photoswitchable inhibitors type 1 fimbriae-mediated adhesion E. coli. An mannobioside 2 was prepared its photochromic properties were investigated. The E→Z isomerisation found be highly effective, yielding a long-lived (Z)-isomer. Both isomers, E Z, show excellent water solubility tested mannoside-specific in solution. Their inhibitory potency equal almost two orders magnitude higher than that the standard inhibitor methyl mannoside. These findings could rationalised on basis computer-aided docking studies. new have qualified this glycoside eventually employed solid support, fabricate adhesive surfaces.