A Fully Solid-Phase Synthesis of Biotinylated Glycoclusters

ABSTRACT

The fully solid-phase synthesis of chemically well-defined glycoclusters grafted to a topological cyclodecapeptide template is described. The orthogonally protected peptide backbone was first synthesized and cyclized on solid support using D-glutamic acid as first amino acid linked to the resin. After successive regioselective deprotection steps, biotins were coupled to the lower addressable domains of the scaffold, then carbohydrates-binding ligands were assembled as cluster on the upper domain using a chemoselective oxime-based strategy. This provides multitopic labeled glycopeptides which can be easily immobilized to streptavidin-coated surfaces for studying carbohydrate-protein interactions in glycomic researches.