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Abstract
A new series of tetravalent glycocyclopeptides has been prepared using the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). When compared with our oximation procedure previously described, we found that the CuAAC strategy led to glycoclusters with similar yield and purity. In addition, the binding properties of these two series of glycoclusters (i.e., with oxime or triazole linkage) were studied with several lectins. Interestingly, while no difference of binding was observed with the mannose-specific lectin from Canavalia ensiformis (ConA), the compound displaying αFuc through oxime linkage has revealed a significant binding improvement with the fucose-specific lectin from Ulex europaeus (UEA-I).
ACKNOWLEDGEMENTS
This work was supported by the University of Grenoble, the Centre National de la Recherche Scientifique (CNRS), and the COST Chemistry project D34. We are grateful to the NanoBio program for access to the facilities of the Synthesis platform. We thank Prof. Julian Garcia for his precious help in the product characterizations by NMR spectroscopy.
