Synthesis and application of branched type II arabinogalactans

Mathias Christian Franch Andersen, Irene Boos, Colin Ruprecht, William G. T. Willats, Fabian Pfrengle, Mads Hartvig Clausen

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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 mono- 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.
Original languageEnglish
JournalJournal of organic chemistry
Volume82
Issue number23
Pages (from-to)12066–12084
ISSN0022-3263
DOIs
Publication statusPublished - 2017

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