Abstract
Glycans (carbohydrate portion of glycoproteins and glycolipids) frequently exert their function through oligomeric interactions involving multiple carbohydrate units. In efforts to recapitulate the diverse spatial arrangements of the carbohydrate units, assemblies based on hybridization of nucleic acid conjugates have been used to display simplified ligands with tailored interligand distances and valences. The programmability of the assemblies lends itself to a combinatorial display of multiple ligands. Recent efforts in the synthesis and applications of such conjugates are discussed.
Highlights
Cell surface glycans are important actors in cellular recognition and have been implicated in numerous events such as fertilization, embryonic development, lymphocyte trafficking and cancer metastasis [1,2,3,4]
Our first efforts in the area of glycan display aimed to demonstrate that a DNA template could be used to program the assembly of discrete peptide nucleic acid (PNA)-tagged ligands in order to recapitulate the geometry of HIV’s gp120 glycan epitope which is composed of multiple copies of a high mannose undecasaccharide [38]
This work led to the discovery of a high-affinity ligand (KD = 82 nM) that was effective at inhibiting bacterial penetration in epithelial cells. It is well-established that nucleic acid-based assemblies can be used to display glycans with a synergy between the interactions of the individual ligands binding with a target
Summary
Cell surface glycans are important actors in cellular recognition and have been implicated in numerous events such as fertilization, embryonic development, lymphocyte trafficking and cancer metastasis [1,2,3,4]. The different assemblies were tested for their binding affinity to the RCA120 lectin showing a correlation between affinity and the inter-galactose distance establishing that DNA display of glycans can be used to tune the optimal spatial arrangement of the ligands in synergic interactions. The generality of this method was illustrated with the synthesis of 16 different DNA conjugates containing one or two glycan units.
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