Facile synthesis of chain-end functionalized glycopolymers for site-specific bioconjugation

Bioconjugate Chemistry
Sijian HouElliot L Chaikof

Abstract

A series of derivatized arylamine initiators were used to generate chain-end functionalized glycopolymers by cyanoxyl-mediated free-radical polymerization. Significant features of this strategy include the capacity to produce polymers of low polydispersity (PDI < 1.5) under aqueous conditions using unprotected monomers bearing a wide range of functional groups. In addition, the presence of a phenyl ring simplifies calculation of polymer saccharide content and molar mass by (1)H NMR. It is particularly noteworthy, however, that derivatized arylamine initiators in conjunction with the presence of a terminal cyanate group provide a convenient approach for synthesizing polymers with a variety of distinct functional groups at alpha and omega chain ends. In the process, the capacity to label glycopolymers or otherwise conjugate them to proteins or other molecules is greatly enhanced.

References

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Jan 9, 1999·Glycoconjugate Journal·N V Bovin
Feb 14, 2002·Chemical Reviews·Joseph J Lundquist, Eric J Toone
Jun 11, 2002·Analytical Biochemistry·Jason E GestwickiLaura L Kiessling
Jun 20, 2002·Journal of the American Chemical Society·Xue-Long SunElliot L Chaikof

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Citations

Sep 22, 2005·Chemical Communications : Chem Comm·Debora BontempoHeather D Maynard
Dec 2, 2015·Biomacromolecules·Franka EnnenDietmar Appelhans
Oct 21, 2014·Biomacromolecules·Yongshun HuangNeil Ayres
Oct 16, 2014·Bioconjugate Chemistry·En-Wei LinHeather D Maynard
Nov 25, 2014·Journal of Carbohydrate Chemistry·Valentinas GruzdysXue-Long Sun
Oct 1, 2013·The Journal of Organic Chemistry·Amit WaliaRichard B Silverman
Oct 16, 2016·Biomacromolecules·Samantha J PaluckHeather D Maynard
Feb 1, 2018·Macromolecular Rapid Communications·Yuanyuan JuHanying Zhao
Nov 22, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Petr NiederhafnerJan Jezek
Sep 8, 2010·Chembiochem : a European Journal of Chemical Biology·Srinivas ChalagallaXue-Long Sun
Dec 14, 2006·Organic & Biomolecular Chemistry·Karina L Heredia, Heather D Maynard
Dec 22, 2009·Chemical Society Reviews·Luiz A CanalleJan C M van Hest
Nov 8, 2012·Chembiochem : a European Journal of Chemical Biology·Vimary Vázquez-DorbattHeather D Maynard

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