Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation

Journal Publication ResearchOnline@JCU
Weaver, Lucy G.;Singh, Yogendra;Vamvounis, George;Wyatt, Mark F.;Burn, Paul L.;Blanchfield, Joanne T.
George Vamvounis
Abstract

A convergent synthesis of a first generation dendrimer with biphenyl-based dendrons and a hexaphenylbenzene core is reported. Suzuki coupling of six first generation biphenyl-dendrons with the rigid hexakis(4-iodophenyl)benzene core furnished the title asterisk-cored dendrimer in 60% yield. Twelve copies of β-(1→6)-linked glucosamine-based oligosaccharides were then efficiently coupled with the acetylenyl surface groups of the dendrimer via a Huisgen 1,3-dipolar cycloaddition reaction to give a series of multivalent carbohydrate constructs that mimic the globular nodules of polysaccharide intercellular adhesin (PIA) produced by Staphylococcus aureus.

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5

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1759-9962

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Pages Count

7

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Royal Society of Chemistry

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DOI

10.1039/C3PY01123B