Abstract
This paper reports the production of glycopolymers via a simple and flexible method. A novel glycopolymer with a hyperbranched poly(amido amine) core and a sugar shell (HPAA-GLc) was synthesized by using thiol-ene click reaction via facile one-pot method. Hyperbranched poly(amido amine) with vinyl terminals was first synthesized by Michael addition polymerization of N,N′-methylene bisacrylamide (MBA) with 1-(2-aminoethyl) piperazine (AEPZ). Subsequently, thiol-ene click reaction between vinyl units of hyperbranched poly(amido amine) and thio-glucose was performed in situ. Based on the NMR result, all the vinyl groups reacted with thiol-glucose in 120 min. Strong photoluminescence emission was observed from the aqueous solution of HPAA-GLc.
Similar content being viewed by others
References
Hoyle CE, Lee, TY, Roper T. Thiol-enes: Chemistry of the past with promise for the future. J Polym Sci Part A: Polym Chem, 2004, 42: 5301–5338
Hoyle CE, Bowman CN. Thiol-ene click chemistry. Angew Chem Int Ed, 2010, 49: 1540–1573
Dondoni A. The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry. Angew Chem Int Ed, 2008, 47: 8995–8997
Iha RK, Wooley KL, Nystrom AM, Burke DJ, Kade MJ, Hawker CJ. Applications of orthogonal “click” chemistries in the synthesis of functional soft materials. Chem Rev, 2009, 109: 5620–5686
Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angew Chem Int Edit, 2001, 40: 2004–2021
Chen GJ, Amajjahe S, Stenzel MH. Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier. Chem Commun, 2009, 1198–1200
Semsarilar M, Ladmiral V, Perrier S. Highly branched and hyperbranched glycopolymers via reversible addition-fragmentation chain transfer polymerization and click chemistry. Macromolecules, 2010, 43: 1438–1443
Spain SG, Gibson MI, Cameron NR. Recent advances in the synthesis of well-defined glycopolymers. J Polym Sci Part A: Polym Chem, 2007, 45: 2059–2072
Ladmiral V, Melia E, Haddleton DM. Synthetic glycopolymers: An overview. Eur Polym J, 2004, 40: 431–449
Goa KL, Benfield P. Hyaluronic acid: A review of its pharmacology and use as a surgical aid in ophthalmology, and its therapeutic potential in joint disease and wound-healing. Drugs, 1994, 47: 536–566
McAlindon TE, LaValley MP, Gulin JP, Felson DT. Glucosamine and chondroitin for treatment of osteoarthritis — A systematic quality assessment and meta-analysis. Jama-J Am Med Assoc, 2000, 283: 1469–1475
Dove A. The bittersweet promise of glycobiology. Nat Biotechnol, 2001, 19: 913–917
Dwek RA. Glycobiology: Toward understanding the function of sugars. Chem Rev, 1996, 96: 683–720
Sigal GB, Mammen M, Dahmann G, Whitesides GM. Polyacrylamides bearing pendant alpha-sialoside groups strongly inhibit agglutination of erythrocytes by influenza virus: The strong inhibition reflects enhanced binding through cooperative polyvalent interactions. J Am Chem Soc, 1996, 118: 3789–3800
Takasu A, Takada M, Itou H, Hirabayashi T, Kinoshita T. Accelerated biodegradation of poly(vinyl alcohol) by glycosidations of the hydroxyl groups or addition of sugars. Biomacromolecules, 2004, 5: 1029–1037
Ladmiral V, Mantovani G, Clarkson GJ, Cauet S, Irwin JL, Haddleton DM. Synthesis of neoglycopolymers by a combination of “click chemistry” and living radical polymerization. J Am Chem Soc, 2006, 128: 4823–4830
Thibault RJ, Takizawa K, Lowenheilm P, Helms B, Mynar JL, Frechet JMJ, Hawker CJ. A versatile new monomer family: Functionalized 4-vinyl-1,2,3-triazoles via click chemistry. J Am Chem Soc, 2006, 128: 12084–12085
Gamblin DP, Garnier P, van Kasteren S, Oldham NJ, Fairbanks AJ, Davis BG. Glyco-SeS: Selenenylsulfide-mediated protein glycoconjugation — A new strategy in post-translational modification. Angew Chem Int Ed, 2004, 43: 828–833
Floyd N, Vijayakrishnan B, Koeppe AR, Davis BG. Thiyl glycosylation of olefinic proteins: S-linked glycoconjugate synthesis. Angew Chem Int Edit, 2009, 48: 7798–7802
You YZ, Hong CY, Pan CY. Facile one-pot approach for preparing dually responsive core-shell nanostructure. Macromolecules, 2009, 42: 573–575
Zhang YW, Huang W, Zhou YF, Yan DY. A physical gel made from hyperbranched polymer gelator. Chem Commun, 2007, 2587–2589
Wang D, Liu Y, Hong CY, Pan CY. Preparation and characterization of novel hyperbranched poly(amido amine)s from Michael addition polymerizations of trifunctional amines with diacrylamides. J Polym Sci Part A: Polym Chem, 2005, 43: 5127–5137
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yu, Z., Cui, M., Yan, J. et al. One-pot synthesis of hyperbranched poly(amido amine) clicked with a sugar shell via Michael addition polymerization and thiol click reaction. Sci. China Chem. 53, 1663–1668 (2010). https://doi.org/10.1007/s11426-010-4050-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-010-4050-8