Abstract
We describe a protocol for the preparation of glycopolymers derived from the ring-opening polymerization of a norbornene carboxylic acid derivative. Polymerization is followed by attachment of a linker and subsequent glycoconjugation via a triazole-forming azide-alkyne click reaction. The use of a protected amine-terminating agent allows for the attachment of a probe molecule such as a fluorescein dye. The syntheses of a neutral galactopolymer as well a polyanionic poly-3-O-sulfo-galactopolymer are described.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Kiessling LL, Grim JC (2013) Glycopolymer probes of signal transduction. Chem Soc Rev 42:4476–4491
Gestwicki JE, Strong LE, Kiessling LL (2000) Tuning chemotactic responses with synthetic multivalent ligands. Chem Biol 7:583–591
Sheng GJ, Oh YI, Chang S-K, Hsieh-Wilson LC (2013) Tunable heparan sulfate mimetics for modulating chemokine activity. J Am Chem Soc 135:10898–10901
Okoth R, Basu A (2013) End-labeled amino terminated monotelechelic glycopolymers generated by ROMP and Cu(I)-catalyzed azide–alkyne cycloaddition. Beilstein J Org Chem 9:608–612
Love JA, Morgan JP, Trnka TM, Grubbs RH (2002) A practical and highly active ruthenium-based catalyst that effects the cross metathesis of acrylonitrile. Angew Chem Int Edit 41:4035–4037
Zhao J, Liu Y, Park HJ, Boggs JM, Basu A (2012) Carbohydrate-coated fluorescent silica nanoparticles as probes for the galactose/3-sulfogalactose carbohydrate–carbohydrate interaction using model systems and cellular binding studies. Bioconjugate Chem 23:1166–1173
Hong V, Presolski SI, Ma C, Finn MG (2009) Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation. Angew Chem Int Edit 48:9879–9883
Chouhan G, James K (2011) CuAAC macrocyclization: high intramolecular selectivity through the use of copper-tris(triazole) ligand complexes. Org Lett 13:2754–2757
Pangborn AB, Giardello MA, Grubbs RH, Rosen RK, Timmers FJ (1996) Safe and convenient procedure for solvent purification. Organometallics 15:1518–1520
Acknowledgement
This work was supported by the National Science Foundation (CHE-0910947).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer Science+Business Media New York
About this protocol
Cite this protocol
Okoth, R., Basu, A. (2016). Glycopolymers Prepared by Ring-Opening Metathesis Polymerization Followed by Glycoconjugation Using a Triazole-Forming “Click” Reaction. In: Sun, XL. (eds) Macro-Glycoligands. Methods in Molecular Biology, vol 1367. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-3130-9_3
Download citation
DOI: https://doi.org/10.1007/978-1-4939-3130-9_3
Publisher Name: Humana Press, New York, NY
Print ISBN: 978-1-4939-3129-3
Online ISBN: 978-1-4939-3130-9
eBook Packages: Springer Protocols