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Issue 4, 2014
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Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation

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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.

Graphical abstract: Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation

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Supplementary files

Article information


Submitted
21 Aug 2013
Accepted
23 Oct 2013
First published
23 Oct 2013

Polym. Chem., 2014,5, 1173-1179
Article type
Paper

Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation

L. G. Weaver, Y. Singh, G. Vamvounis, M. F. Wyatt, P. L. Burn and J. T. Blanchfield, Polym. Chem., 2014, 5, 1173
DOI: 10.1039/C3PY01123B

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