Synthesis and Evaluation of Neoglycoconjugates Based on Adamantyl Scaffolds

Abstract

Lectin–carbohydrate interactions are important for many biological processes of high pharmaceutical interest. Multivalent carbohydrate conjugates (glycoclusters) have been frequently used to study and manipulate these interactions. In this report, we present the synthesis of trimeric glucose and mannose conjugates that have been assembled with an AB3 scaffold based on adamantane. Several neoglycoconjugates bearing three carbohydrates have been synthesized with different ethylene glycol spacers between the sugar moieties and the adamantyl core. An additional orthogonal functionality at the remaining adamantane bridgehead position allows the conjugation of these trimeric cluster glycosides to other functional molecules such as fluorescent dyes or a solid support for the construction of glycoarrays. We have evaluated the binding properties of trivalent carbohydrate derivatives to ConA as a model lectin in solution by STD‐NMR and on a lectin array by using fluorescent glycoconjugates.

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

“…For this reason, the central scaffold should also have a rigid geometry without much conformational flexibility to create a preorganized binding pocket. In this regard, the adamantane scaffold received some attention as it represents a conformationally strained analog of the cyclohexane ring [10][11][12][13]. However, the preparation of trisubstituted adamantanes is challenging because multiple functionalization of the parent hydrocarbon is not selective, while the synthesis from acyclic precursors requires multistep synthetic routes [10,14].…”