title: Synthesis of Chain-End Functionalized Glycopolymers via Cyanoxyl-Mediated Free Radical Polymerization (CMFRP).
abstract: Glycopolymers are often used as glyco-macroligands for biological research and biomedical applications in carbohydrate recognitions. Chain-end functionalized glycopolymers show more potential for practical applications, such as protein modification and solid-phase bioassays. In particular, the chain-end group allows for direct one-to-one attachment or facilitates site-specific and oriented immobilization onto solid surfaces. A series of derivatized arylamine initiators are used to generate chain-end functionalized glycopolymers by cyanoxyl-mediated free radical polymerization (CMFRP). Important 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, it provides a one-pot method to synthesize α,ω-telechelic glycopolymers with derivatized arylamine at one site and O-cyanate at the other site. In the process, the capacity to orthogonally label glycopolymers or otherwise conjugate them to proteins and other molecules is greatly enhanced.
authors.affiliation: Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Ave., Cleveland, OH, 44115, USA.
authors.forename: Valentinas
authors.initials: V
authors.lastname: Gruzdys
authors.affiliation: Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Ave., Cleveland, OH, 44115, USA.
authors.forename: Jinshan
authors.initials: J
authors.lastname: Tang
authors.affiliation: Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Wyss Institute of Biologically Inspired Engineering at Harvard University, Boston, MA, 02115, USA.
authors.forename: Elliot
authors.initials: E
authors.lastname: Chaikof
authors.affiliation: Department of Chemistry, Chemical and Biomedical Engineering and Center for Gene Regulation in Health and Disease (GRHD), Cleveland State University, 2121 Euclid Ave., Cleveland, OH, 44115, USA. x.sun55@csuohio.edu.
authors.forename: Xue-Long
authors.initials: XL
authors.lastname: Sun
mesh_terms: D003485:Cyanates / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis*; D058105:Polymerization; D011108:Polymers / Q000138:chemical synthesis*
chemical_list: D003485:Cyanates; D005609:Free Radicals; D006001:Glycoconjugates; D011108:Polymers
keywords: Biotin; Carbohydrate; Chain-end functionalized; Cyanoxyl-mediated free radical polymerization; Glycopolymer; Lactose