Sequence-Defined Glycopolymer Segments Presenting Mannose: Synthesis and Lectin Binding Affinity

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...

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Published in	Biomacromolecules Vol. 13; no. 6; pp. 1845 - 1852
Main Authors	Ponader, Daniela, Wojcik, Felix, Beceren-Braun, Figen, Dernedde, Jens, Hartmann, Laura
Format	Journal Article
Language	English
Published	Washington, DC American Chemical Society 11.06.2012
Subjects	alkynes Applied sciences binding capacity Binding Sites chemical composition concanavalin A Concanavalin A - chemistry Exact sciences and technology hydrophilicity ligands mannose Mannose - chemistry Organic polymers Physicochemistry of polymers polymers Polymers with particular properties Polysaccharides - chemical synthesis Polysaccharides - chemistry Preparation, kinetics, thermodynamics, mechanism and catalysts surface plasmon resonance Lectin 1,3-Dipolar cycloaddition Nylon Aldose Concanavalin A Experimental study Oligomer Lateral group Monodispersed polymer Chemical modification Aliphatic polymer Preparation Solid state reaction Molecular recognition Glycoside Surface plasmon resonance Peptide synthesis Aqueous solution
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ISSN	1525-7797 1526-4602 1526-4602
DOI	10.1021/bm300331z

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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.
AbstractList	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. 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.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.
Author	Wojcik, Felix Beceren-Braun, Figen Hartmann, Laura Ponader, Daniela Dernedde, Jens
AuthorAffiliation	Charité-Universitätsmedizin MPI of Colloids and Interfaces
AuthorAffiliation_xml	– name: MPI of Colloids and Interfaces – name: Charité-Universitätsmedizin
Author_xml	– sequence: 1 givenname: Daniela surname: Ponader fullname: Ponader, Daniela – sequence: 2 givenname: Felix surname: Wojcik fullname: Wojcik, Felix – sequence: 3 givenname: Figen surname: Beceren-Braun fullname: Beceren-Braun, Figen – sequence: 4 givenname: Jens surname: Dernedde fullname: Dernedde, Jens – sequence: 5 givenname: Laura surname: Hartmann fullname: Hartmann, Laura email: laura.hartmann@mpikg.mpg.de
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Keywords	Lectin 1,3-Dipolar cycloaddition Nylon Aldose Concanavalin A Experimental study Oligomer Lateral group Monodispersed polymer Chemical modification Aliphatic polymer Preparation Solid state reaction Molecular recognition Glycoside Surface plasmon resonance Peptide synthesis Aqueous solution
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Snippet	We present for the first time the synthesis of sequence-defined monodisperse glycopolymer segments via solid-phase polymer synthesis. Functional building...
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SubjectTerms	alkynes Applied sciences binding capacity Binding Sites chemical composition concanavalin A Concanavalin A - chemistry Exact sciences and technology hydrophilicity ligands mannose Mannose - chemistry Organic polymers Physicochemistry of polymers polymers Polymers with particular properties Polysaccharides - chemical synthesis Polysaccharides - chemistry Preparation, kinetics, thermodynamics, mechanism and catalysts surface plasmon resonance
Title	Sequence-Defined Glycopolymer Segments Presenting Mannose: Synthesis and Lectin Binding Affinity
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