Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations.

ABSTRACT

Synthetic heteroglycoclusters are being subjected to increasing interest due to their potential to serve as selective ligands for carbohydrate-binding proteins. In this paper, we describe an expedient strategy to prepare cyclopeptides displaying well-defined distributions and combinations of carbohydrates. By using both oxime ligation and copper(I)-catalyzed alkyne-azide cycloaddition, two series of compounds bearing binary combinations of αMan, αFuc or ßLac in an overall tetravalent presentation, and either 22 or 31 relative proportions, have been prepared.