Schaltung bakterieller Adhäsion auf glycosylierten Oberflächen durch reversible Reorientierung der Kohlenhydratliganden

Joining Hydroxyazobenzene and Mannose under Mitsunobu Conditions

“…During the Mitsunobu reaction with 3 , on the other hand, S N 1 and S N 2 substitution processes are apparently competing, as was discussed previously 14. We will employ this reaction to prepare the β‐configured glycoarray analogues of those photoswitchable surfaces that allowed photocontrol of bacterial adhesion 4. Through the biological testing of a surface, analogous to that tested earlier, we will gain further insight into this novel biological phenomenon.…”

“…Since 2012, our group has contributed to the synthesis and investigation of azobenzene‐based “sweet switches” to study photoswitching of cellular adhesion 3. In fact, we demonstrated very recently that photoisomerization of azobenzene α‐ D ‐mannoside ligands, ligated to a surface, allows us to reversibly switch the carbohydrate‐specific adhesion of live Escherichia coli bacteria to such glycoarrays 4…”

Multivalency at Interfaces: Supramolecular Carbohydrate-Functionalized Graphene Derivatives for Bacterial Capture, Release, and Disinfection

“…value of ManCD towards ORN178 at 117 was much higher than for ORN208 without mannose binding sites (14), as well as for CD@AG4 with ORN178 (18) and ORN208 (16). Without the assistance of the graphene scaffold, the mannosyl-functionalized macrocycle ManCD only slightly induced agglutination (17), which clearly reflected the benefit of the 2D large flexible carbon surface for capturing pathogenic cells. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 13 Multivalent binding and the responsive release potential of ManCD@AG4 towards E. coli were determined using a competition experiment: Co-incubation of the FITC-stained ORN178 E. coli with varying concentrations of the monovalent binder: methyl α-D-mannopyranoside (Me-Man) and ManCD@AG4.…”

“…16 However, soluble multivalent glycolconjugate two-dimensional (2D) scaffolds that have adequate dimensions for biological pathogens can act as potent but elusive inhibitors. 17 4…”