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Facile and Efficient Preparation of Tri-component Fluorescent Glycopolymers via RAFT-controlled Polymerization
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Synthesis and Characterization of α,ω-End Orthogonally Functionalizable Glycopolymers from Native Glycans
Joseph M Keil1, Ka Keung Chan1, Xue-Long Sun1
1Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Avenue, Cleveland, Ohio 44115, United States.
Polymer Chemistry
|December 16, 2024
Summary
We developed a simple method to create functional glycopolymers with distinct reactive ends. These versatile biomaterials enable precise modification for diverse biomedical applications.
Area of Science:
- Biomaterials Science
- Polymer Chemistry
- Glycobiology
Background:
- Glycopolymers serve as biomimetic glycoconjugates in biological and biomedical fields.
- Chain-end functionalized glycopolymers are crucial for applications like protein modification, microarrays, biosensors, and bioprobes.
Purpose of the Study:
- To develop a straightforward synthesis for α,ω-end orthogonally functionalizable glycopolymers.
- To enable versatile bioconjugation strategies using distinct reactive chain ends.
Main Methods:
- Cyanoxyl-mediated free-radical polymerization of native glycans without protection/deprotection.
- Introduction of alkyne or azide groups at one chain end and O-cyanate at the other.
- Utilizing click chemistry and isourea bond formation for orthogonal functionalization.
Main Results:
- Successfully synthesized α,ω-end orthogonally functionalizable glycopolymers.
- Demonstrated site-specific bioconjugation via click chemistry (alkyne-azide) and isourea bond formation (O-cyanate-amine).
- Achieved sequential and one-pot heterofunctionalization, as well as end-to-end dimerization of glycopolymers.
Conclusions:
- The synthesized glycopolymers offer orthogonal functionalization capabilities at both chain ends.
- These versatile glycopolymers are valuable tools for advanced biological and biomedical research and applications.
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