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Published on: June 19, 2015
Synthesis and Application of Branched Type II Arabinogalactans
Mathias C F Andersen1, Irene Boos1, Colin Ruprecht2
1Center for Nanomedicine and Theranostics, Department of Chemistry, Technical University of Denmark , Kemitorvet, Building 207, 2800 Kgs. Lyngby, Denmark.
Abstract:
The synthesis of linear and (1 → 6)-branched β-(1 → 3)-d-galactans, structures found in plant arabinogalactan proteins (AGPs), is described. The synthetic strategy relies on iterative couplings of monosaccharide and disaccharide thioglycoside donors, followed by a late-stage glycosylation of heptagalactan backbone acceptors to introduce branching. A key finding from the synthetic study was the need to match protective groups in order to tune reactivity and ensure selectivity during the assembly. Carbohydrate microarrays were generated to enable the detailed epitope mapping of two monoclonal antibodies known to recognize AGPs: JIM16 and JIM133.
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