Sequence-Defined Glycopolymer
Segments Presenting
Mannose: Synthesis and Lectin Binding Affinity
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Abstract
We present for the first time the synthesis of sequence-defined
monodisperse glycopolymer segments via solid-phase polymer synthesis.
Functional building blocks displaying alkyne moieties and hydrophilic
ethylenedioxy units were assembled stepwise on solid phase. The resulting
polymer segments were conjugated with mannose sugars via 1,3-dipolar
cycloaddition. The obtained mono-, di-, and trivalent mannose structures
were then subject to Con A lectin binding. Surface plasmon resonance
studies showed a nonlinear increase in binding regarding the number
and spacing of sugar ligands. The results of Con A lectin binding
assays indicate that the chemical composition of the polymeric scaffold
strongly contributes to the binding activities as well as the spacing
between the ligands and the number of presented mannose units. Our
approach now allows for the synthesis of highly defined glycooligomers
and glycopolymers with a diversity of properties to investigate systematically
multivalent effects of polymeric ligands