Statistical Glycopolymers Based on 2-Hydroxyethyl Methacrylate: Copolymerization, Thermal Properties, and Lectin Interaction Studies Vanesa Bordege ´, Alexandra Mun ˜oz-Bonilla, Orietta Leo ´n, Rocı ´o Cuervo-Rodrı ´guez, Manuel Sa ´nchez-Chaves, Marta Ferna ´ndez-Garcı ´a* Introduction Carbohydrates play a crucial role in a wide range of biological functions, involving recognition process. Recog- nition is an initiation step in many processes based on cell– cell interactions such as signal transmission, fertilization, inflammation, or immune defenses. [1–5] The saccharides attached to the cell surfaces provide cells with their individuality and recognition patterns, often called ‘‘glycocode,’’ due to specific interaction between carbo- hydrates and protein receptor knows as lectins. Individual saccharide–lectin interactions are weak, increasing the specificity and the binding affinity through multivalent binding process, which is known as cluster glycoside effect. [6–8] To this respect, in recent years, synthetic polymers having saccharides moieties along or at the end of the main chain, so-called glycopolymers, have received an important attention in the biomedical fields. [9–11] Glycopolymers can induce enhancement of binding affinity Full Paper M. Ferna ´ndez-Garcı ´a, V. Bordege ´, A. Mun ˜oz-Bonilla, O. Leo ´n, M. Sa ´nchez-Chaves Departamento de Quı ´mica y Propiedades de Materiales Polime ´ricos, Instituto de Ciencia y Tecnologı ´a de Polı ´meros (CSIC), C/Juan de la Cierva 3, 28006 Madrid, Spain E-mail: martafg@ictp.csic.es R. Cuervo-Rodrı ´guez Departamento de Quı ´mica Orga ´nica I, Facultad de Ciencias Quı ´micas, Universidad Complutense de Madrid, Avenida Complutense s/n, Ciudad Universitaria, 28040 Madrid, Spain Amphiphilic statistical glycopolymers based on unprotected glycomonomer, 2-{[(D-glucosa- min-2-N-yl)carbonyl]oxy}ethyl methacrylate (HEMAGl), and methyl acrylate have been syn- thesized by classical free radical polymerization in DMSO solutions at 70 8C. The reactions have been followed by in situ monitoring proton NMR. The monomer reactivity ratios have been calculated using Kelen-Tu ¨do¨s extended equation. Then, the cumulative feed and copolymer compositions as a function of conversion have been obtained, showing a good agree- ment between the experimental and theoretical data. The thermal properties such as their glass transition and thermal stability temperatures have been ana- lyzed. In addition, the carbohydrate–lectin interaction in those water-soluble glyco- polymers has been studied, demonstrating successful binding. 1294 Macromol. Chem. Phys. 2011, 212, 1294–1304 ß 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim wileyonlinelibrary.com DOI: 10.1002/macp.201100014