Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation

Weaver, Lucy G., Singh, Yogendra, Vamvounis, George, Wyatt, Mark F., Burn, Paul L., and Blanchfield, Joanne T. (2014) Carbohydrate globules: molecular asterisk-cored dendrimers for carbohydrate presentation. Polymer Chemistry, 5. pp. 1173-1179.

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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.

Item ID: 31994
Item Type: Article (Research - C1)
ISSN: 1759-9962
Funders: Australian Research Council (ARC), Engineering and Physical Sciences Research Council (EPSRC), University of Queensland (UQ)
Projects and Grants: ARC Australian Research Fellowship DP1095404, EPSRC grant no. EP/F014341/1
Date Deposited: 28 May 2014 00:36
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 50%
03 CHEMICAL SCIENCES > 0303 Macromolecular and Materials Chemistry > 030306 Synthesis of Materials @ 50%
SEO Codes: 92 HEALTH > 9204 Public Health (excl. Specific Population Health) > 920412 Preventive Medicine @ 100%
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