Beilstein J. Org. Chem.2013,9, 223–233, doi:10.3762/bjoc.9.26
adhesive surfaces.
Keywords: azobenzeneglycosides; 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
) in order to make a photoswitchable FimH antagonist available. Photoirradiation of azobenzeneglycosides at ~365 nm effects E→Z isomerisation of the N=N double bond, and thermal relaxation or irradiation at ~450 nm leads to Z→E back isomerisation [13][14]. In the case that the E→Z isomerisation
, glycosylation of the key intermediate 10 by using the mannosyl donor 3 gave the desired mannobioside 11 in 76% yield. Finally, removal of the O-acetyl groups according to Zemplén led to the unprotected 1,3-linked target mannobioside α-D-Man-(1→3)-D-Man (2).
With the two azobenzeneglycosides 6 and 2 at hand
PDF
Graphical Abstract
Figure 1:
The α-(1→3)-linked mannobioside α-D-Man-(1→3)-D-Man 1 (B) is a potent disaccharide ligand for the b...