title: Preparation of amphiphilic glycopolymers with flexible long side chain and their use as stabilizer for emulsion polymerization.
abstract: A glycomonomer was synthesized from poly(ethylene glycol) methacrylate (PEGMA). The terminal hydroxyl moieties were activated with ester groups and subsequently the glucosamine was incorporated forming urethane linkages. The obtained glycomonomer was copolymerized with methyl acrylate by free radical polymerization varying the initial feed composition to produce different amphiphilic glycopolymers. The glycopolymers were then characterized and compared with the homologous glycopolymers based on 2-{[(D-glucosamin-2-N-yl)carbonyl]oxy}ethyl methacrylate. Both series of glycopolymers were used in emulsion polymerization of methyl acrylate as stabilizers without the addition of any cosurfactant. Although high conversions were not achieved with any of the employed surfactant, the glycopolymers provide good colloidal stability, spherical, monodisperse and small latex particles in comparison with the surfactant-free emulsion polymerization. The latex particles stabilized with the glycosurfactant based on PEGMA, containing a flexible spacer between the backbone and the glucosamine, lead to smooth films whereas the short side chain surfactant from 2-hydroxyethyl methacrylate (HEMA), with higher glass transition temperature, restricts the coalescence of particles and, therefore, the film formation. Moreover, the surface bioactivity of these polymer coatings was examined by analyzing their specific interaction with the lectin, Concanavalin A, Canavalia ensiformis. The specific and successful binding to the Concanavalin A was demonstrated by fluorescence microscopy for both series being more intense with increasing amount of glycounits in the glycopolymer stabilizers. Interestingly, the incorporation of a flexible spacer in the glycopolymer structures enhances the binding activity.
authors.affiliation: Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Marta
authors.initials: M
authors.lastname: Alvárez-Paino
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Avenida Complutense s/n, Ciudad Universitaria, 28040 Madrid, Spain.
authors.forename: Rafael
authors.initials: R
authors.lastname: Juan-Rodríguez
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Avenida Complutense s/n, Ciudad Universitaria, 28040 Madrid, Spain.
authors.forename: Rocío
authors.initials: R
authors.lastname: Cuervo-Rodríguez
authors.affiliation: Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain. Electronic address: sbonilla@ictp.csic.es.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Muñoz-Bonilla
authors.affiliation: Instituto de Ciencia y Tecnología de Polímeros (ICTP-CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain. Electronic address: martafg@ictp.csic.es.
authors.forename: Marta
authors.initials: M
authors.lastname: Fernández-García
mesh_terms: D000179:Acrylates / Q000737:chemistry; D003102:Colloids; D003208:Concanavalin A / Q000737:chemistry*; D004655:Emulsions; D005944:Glucosamine / Q000737:chemistry*; D007840:Latex / Q000737:chemistry; D008689:Methacrylates / Q000737:chemistry*; D008856:Microscopy, Fluorescence; D010316:Particle Size; D011092:Polyethylene Glycols / Q000737:chemistry*; D058105:Polymerization; D011485:Protein Binding; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D000179:Acrylates; D003102:Colloids; D004655:Emulsions; D007840:Latex; D008689:Methacrylates; D013501:Surface-Active Agents; C524499:polyethylene glycol methacrylate; D003208:Concanavalin A; D011092:Polyethylene Glycols; C005044:hydroxyethyl methacrylate; D005944:Glucosamine; C035956:methyl acrylate
keywords: Biomolecular recognition; Film formation; Glycopolymer surfactant; Latex particles