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Issue 11, 2013
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Multivalent glycoconjugate syntheses and applications using aromatic scaffolds

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Abstract

Glycan–protein interactions are of utmost importance in several biological phenomena. Although the variety of carbohydrate residues in mammalian cells is limited to less than a dozen different sugars, their spatial topographical presentation in what is now associated as the “glycocodes” provides the fundamental keys for specific and high affinity “lock-in” recognition events associated with a wide range of pathologies. Toward deciphering our understanding of these glycocodes, chemists have developed new creative tools that included dendrimer chemistry in order to provide monodisperse multivalent glycoconjugates. This review provides a survey of the numerous aromatic architectures generated for the multivalent presentation of relevant carbohydrates using covalent attachment or supramolecular self-assemblies. The basic concepts toward their controlled syntheses will be described using modern synthetic procedures with a particular emphasis on powerful organometallic methodologies. The large variety of dendritic aromatic scaffolds, together with a brief survey of their unique biophysical and biological properties will be critically reviewed. The distinctiveness of the resulting multivalent glycoarchitectures, encompassing glycoclusters, glycodendrimers and molecularly defined self-assemblies, in forming well organized cross-linked lattices with multivalent carbohydrate binding proteins (lectins) together with their photophysical, medical, and imaging properties will also be briefly highlighted. The topic will be presented in increasing order of aromatic backbone complexities and will end with fullerenes together with self-assembled nanostructures, thus complementing the various scaffolds described in this special thematic issue dedicated to multivalent glycoscience.

Graphical abstract: Multivalent glycoconjugate syntheses and applications using aromatic scaffolds

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Publication details

The article was received on 27 Nov 2012 and first published on 12 Feb 2013


Article type: Review Article
DOI: 10.1039/C3CS35483K
Citation: Chem. Soc. Rev., 2013,42, 4657-4708
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    Multivalent glycoconjugate syntheses and applications using aromatic scaffolds

    Y. M. Chabre and R. Roy, Chem. Soc. Rev., 2013, 42, 4657
    DOI: 10.1039/C3CS35483K

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