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Heteromultivalent Glycooligomers as Mimetics of Blood Group Antigens
Author(s) -
Bücher Katharina S.,
Konietzny Patrick B.,
Snyder Nicole L.,
Hartmann Laura
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804505
Subject(s) - alkyne , cycloaddition , glycan , chemistry , lectin , branching (polymer chemistry) , epitope , moiety , combinatorial chemistry , carbohydrate , solid phase synthesis , azide , click chemistry , blood group antigens , antigen , glycoprotein , biochemistry , stereochemistry , peptide , biology , organic chemistry , immunology , catalysis
Abstract Precision glycomacromolecules have proven to be important tools for the investigation of multivalent carbohydrate–lectin interactions by presenting multiple glycan epitopes on a highly‐defined synthetic scaffold. Herein, we present a new strategy for the versatile assembly of heteromultivalent glycomacromolecules that contain different carbohydrate motifs in proximity within the side chains. A new building block suitable for the solid‐phase polymer synthesis of precision glycomacromolecules was developed with a branching point in the side chain that bears a free alkyne and a TIPS‐protected alkyne moiety, which enables the subsequent attachment of different carbohydrate motifs by on‐resin copper‐mediated azide–alkyne cycloaddition reactions. Applying this synthetic strategy, heteromultivalent glycooligomers presenting fragments of histo‐blood group antigens and human milk oligosaccharides were synthesized and tested for their binding behavior towards bacterial lectin LecB.