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Issue 11, 2013
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Glycoclusters on oligonucleotide and PNA scaffolds: synthesis and applications

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Conjugation of oligonucleotides (ONs) to a variety of reporter groups has been the subject of intensive research during the last decade. Conjugation is indeed of great interest because it can be used not only to improve the existing ONs properties but also to impart new ones. In this context tremendous efforts have been made to conjugate carbohydrate moieties to ONs. Indeed carbohydrates play an important role in biological processes such as signal transduction and cell adhesion through the recognition with sugar-binding proteins (i.e. lectins) located on the surface of cells. For this reason, carbohydrateoligonucleotide conjugates (COCs) have been first developed for improving the poor cellular uptake or tissue specific delivery of ONs through receptor-mediated endocytosis. Besides the targeted ONs delivery, carbohydrate–oligonucleotide conjugates (COCs) are also evaluated in the context of carbohydrate biochips in which surface coating with carbohydrates is achieved by using the DNA-directed immobilization strategy (DDI). Peptide nucleic acids (PNAs) have also been extensively investigated as a surrogate of DNA for diverse applications. Therefore attachment of carbohydrate moieties to this class of molecules has been studied. The aforementioned applications of COCs require mimicking of the natural processes, in which the weak individual protein–carbohydrate binding is overcome by using multivalent interactions. This tutorial review focuses on the recent advances in carbohydrate–oligonucleotide conjugates and describes the major synthetic approaches available. In addition, an overview of applications that have been developed using various scaffolds allowing multivalent interactions is provided. Finally recent results on the use of peptide nucleic acids as oligonucleotides surrogate are described.

Graphical abstract: Glycoclusters on oligonucleotide and PNA scaffolds: synthesis and applications

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Article information

02 Oct 2012
First published
19 Dec 2012

Chem. Soc. Rev., 2013,42, 4557-4573
Article type
Tutorial Review

Glycoclusters on oligonucleotide and PNA scaffolds: synthesis and applications

N. Spinelli, E. Defrancq and F. Morvan, Chem. Soc. Rev., 2013, 42, 4557
DOI: 10.1039/C2CS35406C

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