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André, Sabine; Grandjean, Cyrille; Gautier, François-Moana; Bernardi, Silvia; Sansone, Francesco; Gabius, Hans-Joachim and Ungaro, Rocco (2011): Combining carbohydrate substitutions at bioinspired positions with multivalent presentation towards optimising lectin inhibitors: case study with calixarenes. In: Chemical Communications, Vol. 47, No. 21: pp. 6126-6128 [PDF, 818kB]


Carbohydrate derivatisation and glycocluster formation are both known to enhance avidity for lectin binding. Using a plant toxin and human adhesion/growth-regulatory lectins (inter- and intrafamily comparisons) the effect of their combination is examined. In detail, aromatic substituents were introduced at the 2-N or 30-positions of N-acetyllactosamine and the products conjugated to two types of calix[n]arenes (n=4, 6) via thiourealinker chemistry.

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