Facile synthesis of chain-end functionalized glycopolymers for site-specific bioconjugation.
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.
Hou
Sijian
S
Laboratory for Biomolecular Materials Research, Department of Surgery, Emory University School of Medicine, Atlanta, Georgia 30322, USA.
Sun
Xue-Long
XL
Dong
Chang-Ming
CM
Chaikof
Elliot L
EL
D001665:Binding Sites / Q000502:physiology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D011108:Polymers / Q000138:chemical synthesis* / Q000378:metabolism; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000378:metabolism
D011108:Polymers; D011134:Polysaccharides