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Preformed poly(propylene imine) dendrimers (DAB-dendr-(NH2)x) and polyaminoamide dendrimers (PAMAM dendrimers) have been used for the facile construction of high-molecular weight carbohydrate-coated dendrimers (glycodendrimers). Modification of the primary amino end groups of DAB-dendr-(NH2)x and PAMAM dendrimers has been achieved by means of an efficient attachment of spacer-armed derivatives of D-galactose, lactose, tris(ß-D-galactopyranosyloxymethyl) aminomethane, N-acetylneuraminic acid, and a-D-galactosyl-(13)-a-D-galactose (B-disaccharide) via amide bond formation. Alternatively, carbohydrate-containing dendrimers have been synthesised by the convergent growth approach. This synthetic strategy involves the construction of a saccharide cluster which is then used, in combination with a branching component, for the preparation of large dendritic wedges followed by an attachment to a central core. Several glycodendrimers having 9, 18, and 36 D-glucose or D-mannose residues have been synthesised by this route. The regularity of carbohydrate-coated dendrimers has been proved by a variety of chromatographic and spectroscopic techniques, including NMR spectroscopy and MALDI-TOF mass spectrometry. Modelling of the structure of carbohydrate-coated dendrimers by means of molecular dynamics calculations has revealed the globular shape of these macromolecules with carbohydrate residues exposed at their surfaces. Hydrodynamic studies of some synthetic glycodendrimers confirmed these structural models. Evaluation of binding abilities of D-mannose and B-disaccharide-coated dendrimers towards Concavalin A and anti-B antibodies respectively demonstrated a high activity of glycodendrimers when they are used as ligands in interactions with protein receptors. Both modification of preformed dendrimers with biologically-active carbohydrates and the convergent construction of dendritic systems incorporating saccharide residues affords new and simple approaches to high-molecular weight compounds which may be considered as neoglycoconjugates with perfectly symmetrical structures. They hold much promise as multivalent ligands involved in carbohydrate-protein interactions. The combination of the carbohydrate cluster effect with the potential ability of dendritic interior to encapsulate small molecules could be the basis for creating new therapeutics in the field of drug design.
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