Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
Sassaki, G. L., Elli, S., Rudd, T. R., Macchi, E., Yates, E. a., Naggi, A., Shriver, Z., Raman, R., Sasisekharan, R., Torri, G. & Guerrini, M. Human (α2→6) and avian (α2→3) sialylated receptors of influenza A virus show distinct conformations and dynamics in solution. Biochemistry 52, 7217–7230 (2013).
Lee, R. T. & Lee, Y. C. Affinity enhancement by multivalent lectin-carbohydrate interaction. Glycoconj. J. 17, 543–551 (2001).
Cecioni, S. & Imberty, A. Glycomimetics versus multivalent glycoconjugates for the design of high affinity lectin ligands. Chem. Rev. 115, 525–561 (2014).
Vázquez-Dorbatt, V., Lee, J., Lin, E.-W. & Maynard, H. D. Synthesis of glycopolymers by controlled radical polymerization techniques and their applications. Chembiochem 13, 2478–2487 (2012).
Kiessling, L. L. & Grim, J. C. Glycopolymer probes of signal transduction. Chem. Soc. Rev. 42, 4476–4491 (2013).
Malkoch, M., Thibault, R. J., Drockenmuller, E., Messerschmidt, M., Voit, B., Russell, T. P. & Hawker, C. J. Orthogonal approaches to the simultaneous and cascade functionalization of macromolecules using click chemistry. J. Am. Chem. Soc. 127, 14942–14949 (2005).
Slavin, S., Burns, J., Haddleton, D. M. & Becer, C. R. Synthesis of glycopolymers via click reactions. Eur. Polym. J. 47, 435–446 (2011).
Vinson, N., Gou, Y., Becer, C. R., Haddleton, D. M. & Gibson, M. I. Optimised ‘click’ synthesis of glycopolymers with mono/di- and trisaccharides. Polym. Chem. 2, 107–113 (2011).
Gou, Y., Geng, J., Richards, S. J., Burns, J., Remzi Becer, C. & Haddleton, D. M. A detailed study on understanding glycopolymer library and Con A interactions. J. Polym. Sci. A Polym. Chem 51, 2588–2597 (2013).
Verzola, B., Gelfi, C. & Righetti, P. G. Quantitative studies on the adsorption of proteins to the bare silica wall in capillary electrophoresis. II. Effects of adsorbed, neutral polymers on quenching the interaction. J. Chromatogr. A 874, 293–303 (2000).
Seto, H., Takara, M., Yamashita, C., Murakami, T., Hasegawa, T., Hoshino, Y. & Miura, Y. Surface modification of siliceous materials using maleimidation and various functional polymers synthesized by reversible addition-fragmentation chain transfer polymerization. ACS Appl. Mater. Interfaces 4, 5125–5133 (2012).
Ibricevic, A., Pekosz, A., Walter, M. J., Newby, C., Battaile, J. T., Brown, E. G., Holtzman, M. J. & Brody, S. L. Influenza virus receptor specificity and cell tropism in mouse and human airway epithelial cells. J. Virol. 80, 7469–7480 (2006).
Waldmann, M., Jirmann, R., Hoelscher, K., Wienke, M., Niemeyer, F. C., Rehders, D. & Meyer, B. A nanomolar multivalent ligand as entry inhibitor of the hemagglutinin of avian influenza. J. Am. Chem. Soc. 136, 783–788 (2014).
Sigal, G. B., Mammen, M., Dahmann, G. & Whitesides, G. M. Polyacrylamides bearing pendant/α-sialoside groups strongly inhibit agglutination of erythrocytes by influenza virus: The strong inhibition reflects enhanced binding through cooperative polyvalent interactions. J. Am. Chem. Soc. 118, 3789–3800 (1996).
Choi, S. K., Mammen, M. & Whitesides, G. M. Generation and in situ evaluation of libraries of poly(acrylic acid) presenting sialosides as side chains as polyvalent inhibitors of influenza- mediated hemagglutination. J. Am. Chem. Soc. 119, 4103–4111 (1997).
Landers, J. J., Cao, Z., Lee, I., Piehler, L. T., Myc, P. P., Myc, A., Hamouda, T., Galecki, A. T. & Baker, J. R. Prevention of influenza pneumonitis by sialic Acid-conjugated dendritic polymers. J. Infect. Dis. 186, 1222–1230 (2002).
Thang, S. H., Chong, B. Y. K., Mayadunne, R. T. A, Moad, G. & Rizzardo, E. A novel synthesis of functional dithioesters, dithiocarbamates, xanthates and trithiocarbonates. Tetrahedron Lett. 40, 2435–2438 (1999).
Tanaka, T., Nagai, H., Noguchi, M., Kobayashi, A. & Shoda, S.-I. One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution. Chem. Commun. (Camb) 21, 3378–3379 (2009).
Vitale, G., Valina, A. B., Huang, H., Amunugama, R. & Rodgers, M. T. Solvation of copper ions by acetonitrile. Structures and sequential binding energies of Cu+(CH3CN)(x), x=1-5, from collision-induced dissociation and theoretical studies. J. Phys. Chem. A 105, 11351–11364 (2001).
Ambrosi, M., Cameron, N. R. & Davis, B. G. Lectins: tools for the molecular understanding of the glycocode. Org. Biomol. Chem. 3, 1593–1608 (2005).
Acknowledgements
This work is supported by the Grant-in-Aid for Scientific Research B (15H03818).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Competing interests
The authors declare no conflict of interest.
Additional information
Supplementary Information accompanies the paper on Polymer Journal website
Supplementary information
Rights and permissions
About this article
Cite this article
Nagao, M., Kurebayashi, Y., Seto, H. et al. Synthesis of well-controlled glycopolymers bearing oligosaccharides and their interactions with influenza viruses. Polym J 48, 745–749 (2016). https://doi.org/10.1038/pj.2016.14
Received:
Revised:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1038/pj.2016.14
