TY - JOUR
T1 - Synthesis and application of branched type II arabinogalactans
AU - Andersen, Mathias Christian Franch
AU - Boos, Irene
AU - Ruprecht, Colin
AU - Willats, William G. T.
AU - Pfrengle, Fabian
AU - Clausen, Mads Hartvig
PY - 2017
Y1 - 2017
N2 - 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.
AB - 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.
U2 - 10.1021/acs.joc.7b01796
DO - 10.1021/acs.joc.7b01796
M3 - Journal article
C2 - 29120180
SN - 0022-3263
VL - 82
SP - 12066
EP - 12084
JO - Journal of organic chemistry
JF - Journal of organic chemistry
IS - 23
ER -