One-pot synthesis of hyperbranched poly(amido amine) clicked with a sugar shell via Michael addition polymerization and thiol click reaction

Science China Chemistry

Volumn 53, Issue 8, 2010, Pages 1663-1668

  Yu, Zhiqiang ^a   Cui, Mengmeng ^a   Yan, Junjie ^a   You, Yezi ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Glycopolymers; Hyperbranched poly(amido amine); Photoluminescence; Thiol ene click reaction

Indexed keywords

AQUEOUS SOLUTIONS; CLICK REACTION; GLYCOPOLYMERS; HYPERBRANCHED; IN-SITU; METHYLENE BISACRYLAMIDE; MICHAEL ADDITION POLYMERIZATION; ONE-POT METHOD; ONE-POT SYNTHESIS; PHOTOLUMINESCENCE EMISSION; POLY(AMIDO AMINE); THIOL-ENES; VINYL GROUP;

ADDITION REACTIONS; GLUCOSE; ORGANIC COMPOUNDS; PHOTOLUMINESCENCE; POLYMERIZATION; SOLUTIONS; SUGAR (SUCROSE);

SYNTHESIS (CHEMICAL);

EID: 77957978521     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-010-4050-8     Document Type: Article

References (22)

1. 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
2. Hoyle CE, Bowman CN. Thiol-ene click chemistry. Angew Chem Int Ed, 2010, 49:1540-1573
3. 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
4. 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
5. Kolb HC, Finn MG, Sharpless KB. Click chemistry: Diverse chemical function from a few good reactions. Angew Chem Int Edit, 2001, 40:2004-2021
6. Chen GJ, Amajjahe S, Stenzel MH. Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier. Chem Commun, 2009, 1198-1200
7. 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
8. 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
9. Ladmiral V, Melia E, Haddleton DM. Synthetic glycopolymers: An overview. Eur Polym J, 2004, 40:431-449
10. 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
11. 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
12. Dove A. The bittersweet promise of glycobiology. Nat Biotechnol, 2001, 19:913-917
13. Dwek RA. Glycobiology: Toward understanding the function of sugars. Chem Rev, 1996, 96:683-720
14. 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
15. 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
16. 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
17. Thibault RJ, Takizawa K, Lowenheilm P, Helms B, Mynar JL, Frechet, J M J, 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
18. 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
19. 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
20. You YZ, Hong CY, Pan CY. Facile one-pot approach for preparing dually responsive core-shell nanostructure. Macromolecules, 2009, 42:573-575
21. Zhang YW, Huang W, Zhou YF, Yan DY. A physical gel made from hyperbranched polymer gelator. Chem Commun, 2007, 2587-2589
22. 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