Covalent attachment of biorecognizable sugar ligands in several copies at precise positions of cyclomaltooligosaccharide (cyclodextrin, CD) macrocycles has proven to be an extremely flexible strategy to build multivalent conjugates. The commercial availability of the native CDs in three different sizes, their axial symmetry and the possibility of position- and face-selective functionalization allow a strict control of the valency and spatial orientation of the recognition motifs (glycotopes) in low, medium, high and hyperbranched glycoclusters, including glycodendrimer–CD hybrids. “Click-type” ligation chemistries, including copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC), thiol–ene coupling or thiourea-forming reactions, have been implemented to warrant full homogeneity of the adducts. The incorporation of different glycotopes to investigate multivalent interactions in heterogeneous environments has also been accomplished. Not surprisingly, multivalent CD conjugates have been, and continue to be, major actors in studies directed at deciphering the structural features ruling carbohydrate recognition events. Nanometric glycoassemblies endowed with the capability of adapting the inter-saccharide distances and orientations in the presence of a receptor partner or capable of mimicking the fluidity of biological membranes have been conceived by multitopic inclusion complex formation, rotaxanation or self-assembling. Applications in the fields of sensors, site-specific drug and gene delivery or protein stabilization attest for the maturity of the field.

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Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Highly efficient one-pot reactions of amines and carbon disulfide with α,β-unsaturated compounds were carried out in water under a mild and green procedure with high yields.

One-pot synthesis of dithiocarbamates accelerated in water.

Herein, three new glycopolymers have been synthesized via “click polymerization” to promote nucleic acid delivery in the presence of biological media containing serum. These structures were designed to contain a trehalose moiety to promote biocompatibility, water solubility, and stability against aggregation, amide-triazole groups to enhance DNA binding affinity, and an oligoamine unit to facilitate DNA encapsulation, phosphate neutralization, and interactions with cell surfaces. A 2,3,4,2‘,3‘,4‘-hexa-O-acetyl-6,6‘-diazido-6,6‘-dideoxy-d-trehalose (4) monomer was polymerized via copper(I)-catalyzed azide-alkyne cycloaddition with a series of dialkyne-amide comonomers that contain either one, two, or three Boc-protected secondary amines (7a, 7b, or 7c, respectively). After deprotection, three water-soluble polycations (9a, 9b, or 9c) were obtained with similar degrees of polymerization (n = 56−61) to elucidate the role of amine number on nucleic acid binding, complex formation, stability, and cellular deli...

A. Coste‐Sarguet

Papers

Isothiocyanates and cyclic thiocarbamates of alpha,alpha'-trehalose, sucrose, and cyclomaltooligosaccharides.

Isothiocyanates and Cyclic Thiocarbamates of α,α′‐ Trehalose, Sucrose, and Cyclomaltooligosaccharides.