Synthesis of amphiphilic biodegradable glycocopolymers based on poly(ε-caprolactone) by ring-opening polymerization and click chemistry

Authors

  • Ning Xu,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
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  • Rui Wang,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
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  • Fu-Sheng Du,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
    • Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
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  • Zi-Chen Li

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
    • Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
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Abstract

Amphiphilic, biodegradable block glycopolymers based on poly(ε-caprolactone) (PCL) with various pendent saccharides were synthesized by combination of ring-opening polymerization (ROP) and “click” chemistry. PCL macroinitiators obtained by ROP of ε-caprolactone were used to initiate the ROP of 2-bromo-ε-caprolactone (BrCL) to get diblock copolymers, PCL-b-PBrCL. Reaction of the block copolymers with sodium azide converted the bromine groups in the PBrCL block to azide groups. In the final step, click chemistry of alkynyl saccharides with the pendent azide groups of PCL-b-PBrCL led to the formation of the amphiphilic block glycopolymers. These copolymers were characterized by 1H NMR spectroscopy and gel permeation chromatography. The self-assembly behavior of the amphiphilic block copolymers was investigated using transmission electron microscopy and atomic force microscope, spherical aggregates with saccharide groups on the surface were observed, and the aggregates could bind reversibly with Concanavalin A. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3583–3594, 2009

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