Département de chimie moléculaire

We describe the first one-pot orthogonal strategy to prep. well-defined cyclopeptide-based heteroglycoclusters (hGCs) from glycosyl thiols. Both thiol-chloroactetyl coupling (TCC) and thiol-ene coupling (TEC) have been used to decorate cyclopeptides regioselectively with diverse combination of sugars. We demonstrate that the reaction sequence starting with TCC can be performed one-pot whereas the reverse sequence requires a purifn. step after the TEC reaction. The versatility of this orthogonal strategy has been demonstrated through the synthesis of diverse hGCs displaying alternating binary combinations of $\alpha$-d-Man or $\beta$d-GlcNAc, thus providing rapid access to attractive heteroglycosylated platforms for diverse biol. applications. [on SciFinder(R)]