Synthesis of Glycopolymers

Engineered Carbohydrate-Based Materials for Biomedical Applications: Polymers, Surfaces, Dendrimers, Nanoparticles, and Hydrogels

Volumn , Issue , 2010, Pages 1-118

  Pearson, Samuel ^a   Chen, Gaojian ^a   Stenzel, Martina H ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Controlled living radical polymerization and stable free radical polymerization; Glycopolymer synthesis; Ring Opening Metathesis Polymerization (ROMP)

Indexed keywords

EID: 84886156697     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470944349.ch1     Document Type: Chapter

References (208)

1. Wulff, G., Schmid, J., and Venhoff, T. (1996). The Synthesis of Polymerizable Vinyl Sugars. Macromol. Chem. Phys. 197(1), 259-274.
2. Kossmehl, G., andVolkheimer, J ((1989). Synthesis of PolymerizableHexoseDerivatives. Liebigs Annal. Chem. (11), 1127-1130.
3. Black,W. A. P., Dewar, E. T., and Rutherford, D ((1963). Polymerisation of Unsaturated Derivatives of 1,2:5,6-di-O-isopropylidene-d-glucofuranose. J. Chem. Soc. 4433-4439.
4. Kobayashi, K., and Sumitomo, H ((1980). Speciality Polymers Having Sugar as the Pendant Group: Synthesis, Characterization, and Binding of Organic Solute in Water. Macromolecules 13(2),234-239.
5. Helferich, B., and Duve, G ((1958). Zur Synthese Von Glykosiden, II. Chemische Berichte 91(8), 1790-1793.
6. Chung, D. C., Kostelnik, R. J., and Elias, H. G ((1977). Polymerizable Amphiphiles, 1. Synthesis and Proton Magnetic-Resonance Studies of 3-(4-vinylphenyl)propyl-β-d-glucopyranoside. Die Makromol. Chem 178(3),691-700.
7. Nakaya, T., Memita, M., and Kang, M ((1993). Synthesis and Properties of Vinyl-Polymers Containing Glucose Moieties Attached to the Polymer Backbones with Long Alkyl Chains. J. Macromol. Sci.-Pure Appl. Chem. A30, 349-355.
8. Kohan, G., and Just, G ((1974). Simplified Synthesis of 1,2:5,6-di-O-isopropylidened- mannitol. Synthesis-Stuttgart (3), 192-192.
9. Wulff, G., Schmid, J., and Venhoff, T. P ((1996). The Preparation of New Types of Polymerizable Vinyl Sugars with C C Bonds between Sugar and Double Bond. Macromol. Chem. Phys. 197(4),1285-1299.
10. Wulff, G., Zhu, L., and Schmidt, H ((1997). Investigations on Surface-Modified Bulk Polymers. 1. Copolymers of Styrene with a Styrene Moiety Containing a Sugar Monomer. Macromolecules 30(16), 4533-4539.
11. Wulff, G., and Clarkson, G ((1994). On the Synthesis of C-Glycosyl Compounds Containing Double-Bonds without the Use of Protecting Groups. Carbohydr. Res. 257(1),81-95.
12. Degoede, A., Vanoosterom, M., Vandeurzen, M. P. J., Sheldon, R. A., Vanbekkum, H., and Vanrantwijk, F ((1993). Selective Acylation of Sugar-Derivatives Catalyzed by Immobilized Lipase. In Heterogeneous Catalysis and Fine Chemicals III, Guisnet, M., Barbier, J., Barrault, J., Bouchoule, C., Duprez, D., Perot, G., and Montassier, C., Eds. Amsterdam: Elsevier Science, Vol. 78, pp. 513-520.
13. Gill, I., and Valivety, R ((2000). Enzymatic Glycosylation in Plasticized Glass Phases: A Novel and Efficient Route to O-glycosides. Angew. Chem. Int. Ed. 39(21),3804-3808.
14. Kitazawa, S., Okumura, M., Kinomura, K., and Sakakibara, T ((1990). Syntheses and Properties of Novel Vinyl Monomers Bearing a Glycoside Residue. Chem. Lett. (9), 1733-1736.
15. Wulff, G., and Clarkson, G ((1994). New-Type of Polyvinylsaccharides with N,NDimethylbarbituric Acid as a Linker between Sugar and Styrene Residue. Macromol. Chem. Phys. 195(7),2603-2610.
16. Whistler, R. L., and Goatley, J. L ((1961). Copolymerization of 1-Acrylamido-1-Deoxy-d-Glucitol and of 1-Deoxy-1-Methacrylamido-d-Glucitol with Various Vinyl Monomers. J. Polym. Sci. 50(153), 127-132.
17. Klein, J., and Herzog, D ((1987). Poly(vinylsaccharide)s. 2. Synthesis of Some Poly(vinylsaccharide)s of the Amide Type and Investigation of Their Solution Properties. Makromol. Chem.-Macromol. Chem. Phys. 188(6), 1217-1232;
18. Whistler, R. L., Panzer, H. P., and Roberts, H. J ((1961). 1-Acrylamido-1-Deoxy-d-Glucitol, 1-Deoxy-1-Methacrylamido-d-Glucitol and Their Polymerization. J. Org. Chem. 26(5), 1583-1588.
19. Klein, J., and Begli, A. H ((1989). Poly(vinylsaccharide)s. 5. Synthesis and Characterization of Poly(vinylsaccharide)s of the Amide Type with Disaccharides in the Side-Chain. Makromol. Chem.-Macromol. Chem. Phys. 190(10),2527-2534.
20. Klein, J., Begli, A. H., and Engelke, S ((1989). Synthesis and Characterization of New Poly(vinylsaccharide)s of the Urea Type. Makromol. Chem.-Rapid Commun. 10(12),629-636.
21. Kobayashi, K., Sumitomo, H., and Ina, Y ((1983). A Carbohydrate-Containing Synthetic-Polymer Obtained from N-para-Vinylbenzyl-d-Gluconamide. Polym. J. 15(9), 667-671.
22. Kobayashi, K., Sumitomo, H., and Ina, Y ((1985). Synthesis and Functions of Polystyrene Derivatives Having Pendant Oligosaccharides. Polym. J. 17(4), 567-575.
23. Kobayashi, K., Sumitomo, H., Kobayashi, A., Ishida, M., Nishizawa, S., and Akaike, T ((1985). Interaction between Rat Hepatocytes and Oligosaccharide-Containing Polystyrene Derivatives. Kobunshi Ronbunshu 42(11), 719-724.
24. Kobayashi, A., Akaike, T., Kobayashi, K., and Sumitomo, H. (1986). Enhanced Adhesion and Survival Efficiency of Liver-Cells in Culture Dishes Coated with a Lactose-Carrying Styrene Homopolymer. Makromol. Chem.-Rapid Commun. 7(10),645-650.
25. Hetzer, M.,Chen, G.,Barner-Kowollik,C., and Stenzel,M.H ((2010).Neoglycopolymers Based on 4-Vinyl-1,2,3-Triazole Monomers Prepared by Click Chemistry. Macromol. Biosci. 10(2),119-126.
26. Kimura, S., and Imoto, M ((1961). Synthesis of Polymethacryloyl-d-Glucose and Its Copolymers with Acrylonitrile. Vinyl Polymerization LIV. Makromol. Chem. 50(1),155-160.
27. Roy, R., Tropper, F. D., and Romanowska, A ((1992). New Strategy in Glycopolymer Syntheses. Preparation of Antigenic Water-Soluble Poly(acrylamide-co-p-Acrylamidophenyl-β-Lactoside). Bioconjug. Chem. 3(3),256-261.
28. Nishimura, S.-I., Furuike, T., Matsuoka, K., Maruyama, K., Nagata, K., Kurita, K., Nishi, N., and Tokura, S ((1994). Synthetic Glycoconjugates. 4. Use of ω-(Acrylamido)alkyl Glycosides for the Preparation of Cluster Glycopolymers. Macromolecules 27(18),4876-4880.
29. Furuike, T., Nishi, N., Tokura, S., and Nishimura, S.-I ((1995). Synthetic Glycoconjugates. 6. Preparation and Biochemical Evaluation of Novel Cluster-Type Glycopolymers Containing Gal β(1-4)GlcNAc (N-Acetyllactosamine) Residue. Macromolecules 28(21),7241-7247.
30. Tagawa, K., Sendai, N., Ohno, K., Kawaguchi, T., Kitano, H., and Matsunaga, T ((1999). Recognition of Novel Amphiphiles with Many Pendent Mannose Residues by Con A. Bioconjug. Chem. 10(3),354-360.
31. Carpino, L. A., Ringsdorf, H., and Ritter, H ((1976). Pharmacologically Active Polymers, 10. Preparation and Polymerization of 1-O-(4-Methacryloylaminophenyl)-β-d-Glucopyranoside. Makromol. Chem. 177(5),1631-1635.
32. Kimura, S., and Imoto, M ((1961). Synthesis of polymethacryloyl-d-glucose and its Copolymers with Acrylonitrile-Vinyl Polymerization. Makromol. Chem. 50, 155-160.
33. Carneiro, M. J., Fernandes, A., Figueiredo, C. M., Fortes, A. G., and Freitas, A. M ((2001). Synthesis of Carbohydrate Based Polymers. Carbohydr. Polym. 45(2),135-138.
34. Ambrosi, M., Batsanov, A. S., Cameron, N. R., Davis, B. G., Howard, J. A. K., and Hunter, R ((2002). Influence of Preparation Procedure on Polymer Composition:Synthesis and Characterization of Polymethacrylates Bearing α-d-Glucopyranoside and α-d-Galactopyranoside Residues. J. Chem. Soc., Perkin Trans. 1 (1), 45-52.
35. Ambrosi, M., Cameron, N. R., Davis, B. G., and Stolnik, S ((2005). Investigation of the Interaction between Peanut Agglutinin and Synthetic Glycopolymeric Multivalent Ligands. Org. Biol. Chem. 3(8),1476-1480.
36. Cuervo-Rodrö{dotless}guez, R., Bordegé, V., and Fernöndez-Garöi{dotless}a, M ((2007). Synthesis and Characterization of Novel Glycopolymers Based on Ethyl α-Hydroxymethylacrylate. Carbohydr. Polym. 68(1),89-94.
37. Wulff, G., and Diederichs, H ((1998). Preparation and Polymerization of Water-Soluble Styryl Sugars with C-C Bonds between Sugar and Double Bond. Macromol. Chem. Phys.199(1),141-147.
38. Narain, R., Jhurry, D., and Wulff, G ((2002). Synthesis and Characterization of Polymers Containing Linear Sugar Moieties as Side Groups. Eur. Polym J. 38(2),273-280.
39. Zhou, W.-J., Wilson, M. E., Kurth, M. J., Hsieh, Y.-L., Krochta, J. M., and Shoemaker, C. F ((1997). Synthesis and Properties of a Novel Water-Soluble Lactose-Containing Polymer and Its Cross-Linked Hydrogel. Macromolecules 30(23),7063-7068.
40. Zhou, W.-J., Kurth, M. J., Hsieh, Y.-L., and Krochta, J. M ((1999). Synthesis and Characterization of New Styrene Main-Chain Polymer with Pendant Lactose Moiety through Urea Linkage. Macromolecules 32(17),5507-5513.
41. Kobayashi, K., Tsuchida, A., Usui, T., and Akaike, T ((1997). A New Type of Artificial Glycoconjugate Polymer: A Convenient Synthesis and Its Interaction with Lectins. Macromolecules 30(7),2016-2020.
42. Kim, S.-H., Goto, M., and Akaike, T ((2001). Specific Binding of Glucose-Derivatized Polymers to the Asialoglycoprotein Receptor of Mouse Primary Hepatocytes. J. Biol. Chem. 276(38),35312-35319.
43. Miyachi, A., Dohi, H., Neri, P., Mori, H., Uzawa, H., Seto, Y., and Nishida, Y ((2009). Multivalent Galacto-Trehaloses: Design, Synthesis, and Biological Evaluation Under the Concept of Carbohydrate Modules. Biomacromolecules 10(7),1846-1853.
44. Nishimura, S., Matsuoka, K., Furuike, T., Ishii, S., Kurita, K., and Nishimura, K. M ((1991). Synthetic Glycoconjugates. 2. n-Pentenyl Glycosides as Convenient Mediators for the Syntheses of New Types of Glycoprotein Models. Macromolecules 24(15),4236-4241.
45. Nishimura, S., Matsuoka, K., Furuike, T., Nishi, N., Tokura, S., Nagami, K., Murayama, S., and Kurita, K ((1994). Synthetic Glycoconjugates. 3. An Efficient Synthesis of a Glycoprotein Model Having a Lex-Type Trisaccharide Sequence of Tumor-Associated Carbohydrate Antigen. Macromolecules 27(1),157-163.
46. Wulff, G., Schmidt, H., and Zhu, L. M ((1999). Generating Hydrophilic Surfaces on Standard Polymers after Copolymerizationwith LowAmounts of ProtectedVinyl Sugars. Macromol. Chem. Phys. 200(4),774-782.
47. Miura, Y., Ikeda, T., and Kobayashi, K ((2003). Chemo-Enzymatically Synthesized Glycoconjugate Polymers. Biomacromolecules 4(2),410-415.
48. Albertin, L., Stenzel, M. H., Barner-Kowollik, C., Foster, L. J. R., and Davis, T. P ((2005). Solvent and Oxygen Effects on the Free Radical Polymerization of 6-O-Vinyladipoyl-d-Glucopyranose. Polymer 46(9),2831-2835.
49. Moad, G., and Solomon, D. H ((2006). The Chemistry of Radical Polymerization, 2nd ed. Oxford: Elsevier.
50. Solomon, D. H., Rizzardo, E., and Cacioli, P ((1985). U.S. Pat. 4,581,429.
51. Souaille, M., and Fischer, H ((2001). Rate Enhancement and Retardation Strategies in Living Free Radical Polymerizations Mediated by Nitroxides and Other Persistent Species: A Theoretical Assessment. Macromolecules 35(1),248-261.
52. Hawker, C. J., Bosman, A. W., and Harth, E ((2001). New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations. Chem. Rev. 101(12),3661-3688.
53. Sciannamea, V., Jerome, R., and Detrembleur, C ((2008). In-Situ Nitroxide-MediatedRadical Polymerization (NMP) Processes: TheirUnderstanding andOptimization. Chem. Rev. 108(3),1104-1126.
54. Ohno, K., Tsujii, Y., Miyamoto, T., Fukuda, T., Goto, M., Kobayashi, K., and Akaike, T ((1998). Synthesis of aWell-Defined Glycopolymer by Nitroxide-Controlled Free Radical Polymerization. Macromolecules 31(4),1064-1069.
55. Ohno, K., Fukuda, T., and Kitano, H ((1998). Free Radical Polymerization of a Sugar Residue-Carrying Styryl Monomer with a Lipophilic Alkoxyamine Initiator: Synthesis of a Well-Defined Novel Glycolipid. Macromol. Chem. Phys. 199(10),2193-2197.
56. öotz, H.,Harth,E., Schiller, S. M., Frank, C.W.,Knoll,W., and Hawker,C. J ((2002). Synthesis of Lipo-Glycopolymer Amphiphiles by Nitroxide-Mediated Living Free-Radical Polymerization. J. Polym Sci. Part A: Polym. Chem. 40(20),3379-3391.
57. Ohno, K., Izu, Y., Yamamoto, S., Miyamoto, T., and Fukuda, T ((1999). Nitroxide-Controlled Free Radical Polymerization of a Sugar-Carrying AcryloylMonomer. Macromol. Chem. Phys. 200(7),1619-1625.
58. Chen, Y., and Wulff, G ((2001). Amphiphilic Block Copolymers with Pendent Sugar as Hydrophilic Segments and Their Surface Properties. Macromol. Chem. Phys. 202(17),3273-3278.
59. Chen, Y., and Wulff, G ((2001). Synthesis of Poly(styryl Sugar)s by TEMPO Mediated Free Radical Polymerization. Macromol. Chem. Phys. 202(17),3426-3431.
60. Narumi, A., Matsuda, T., Kaga, H., Satoh, T., and Kakuchi, T ((2002). Synthesis of Amphiphilic Triblock Copolymer of Polystyrene and Poly(4-Vinylbenzyl Glucoside) via TEMPO-Mediated Living Radical Polymerization. Polymer 43(17),4835-4840.
61. Narumi, A., Satoh, T., Kaga, H., and Kakuchi, T ((2001). Glycoconjugated Polymer. 3. Synthesis and Amphiphilic Property of Core-Glycoconjugated Star-Shaped Polystyrene. Macromolecules 35(3),699-705.
62. Ting, S. R. S., Min, E. H., Escalé, P., Save, M., Billon, L., and Stenzel, M. H ((2009). Lectin Recognizable Biomaterials Synthesized via Nitroxide-Mediated Polymerization of a Methacryloyl Galactose Monomer. Macromolecules 42(24),9422-9434.
63. Druliner, J. D ((1991). Living Radical Polymerization Involving Oxygen-Centered Species Attached to Propagating Chain Ends. Macromolecules 24(23),6079-6082.
64. Grande, D., Baskaran, S., and Chaikof, E. L ((2001). Glycosaminoglycan-Mimetic Biomaterials. 2. Alkene- and Acrylate-Derivatized Glycopolymers via Cyanoxyl-Mediated Free-Radical Polymerization. Macromolecules 34(6),1640-1646.
65. Grande, D., Baskaran, S., Baskaran, C., Gnanou, Y., and Chaikof, E. L ((2000). Glycosaminoglycan-Mimetic Biomaterials. 1. Nonsulfated and Sulfated Glycopolymers by Cyanoxyl-Mediated Free-Radical Polymerization. Macromolecules 33(4),1123-1125.
66. Baskaran, S., Grande, D., Sun, X.-L., Yayon, A., and Chaikof, E. L ((2002). Glycosaminoglycan-Mimetic Biomaterials. 3. Glycopolymers Prepared from Alkene-Derivatized Mono- and Disaccharide-Based Glycomonomers. Bioconjug. Chem. 13(6),1309-1313.
67. Guan, R., Sun, X.-L., Hou, S., Wu, P., and Chaikof, E. L ((2004). A Glycopolymer Chaperone for Fibroblast Growth Factor-2. Bioconjug. Chem. 15(1),145-151.
68. Sun, X.-L., Grande, D., Baskaran, S., Hanson, S. R., and Chaikof, E. L ((2002). Glycosaminoglycan Mimetic Biomaterials. 4. Synthesis of Sulfated Lactose-Based Glycopolymers That Exhibit Anticoagulant Activity. Biomacromolecules 3(5),1065-1070.
69. Sun, X.-L., Faucher, K. M., Houston, M., Grande, D., and Chaikof, E. L ((2002). Design and Synthesis of Biotin Chain-Terminated Glycopolymers for Surface Glycoengineering. J. Am. Chem. Soc. 124(25),7258-7259.
70. Hou, S., Sun, X.-L., Dong, C.-M., and Chaikof, E. L ((2004). Facile Synthesis of Chain-End Functionalized Glycopolymers for Site-Specific Bioconjugation. Bioconjug. Chem. 15(5),954-959.
71. Kato, M., Kamigaito, M., Sawamoto, M., and Higashimura, T ((1995). Polymerization of Methyl Methacrylate with the Carbon Tetrachloride/Dichlorotris(triphenylphosphine) Ruthenium(II)/Methylaluminum Bis(2,6-di-tert-butylphenoxide) Initiating System: Possibility of Living Radical Polymerization. Macromolecules 28(5),1721-1723.
72. Wang, J.-S., andMatyjaszewski, K ((1995). Controlled/"Living" Radical Polymerization. Atom Transfer Radical Polymerization in the Presence of Transition-Metal Complexes. J. Am. Chem. Soc. 117(20),5614-5615.
73. Ohno, K., Tsujii, Y., and Fukuda, T ((1998). Synthesis of a Well-Defined Glycopolymer by Atom Transfer Radical Polymerization. J. Polym. Sci. Part A: Polym. Chem. 36(14),2473-2481.
74. Ohno, K., Goto, A., Fukuda, T., Xia, J., and Matyjaszewski, K ((1998). Kinetic Study on the Activation Process in an Atom Transfer Radical Polymerization. Macromolecules 31(8),2699-2701.
75. Liang, Y.-Z., Li, Z.-C., Chen, G.-Q., and Li, F.-M ((1999). Synthesis of Well-Defined Poly[(2-β-d-Glucopyranosyloxy)Ethyl Acrylate] by Atom Transfer Radical Polymerization. Polym. Int. 48(9),739-742.
76. Li, Z.-C., Liang, Y.-Z., Chen, G.-Q., and Li, F.-M ((2000). Synthesis of Amphiphilic Block Copolymers withWell-Defined Glycopolymer Segment by Atom Transfer Radical Polymerization. Macromol. Rapid Commun. 21(7),375-380.
77. Li, Z.-C., Liang, Y.-Z., and Li, F.-M ((1999). Multiple Morphologies of Aggregates from Block Copolymers Containing Glycopolymer Segments. Chem. Commun. 1557-1558.
78. Liang, Y.-Z., Li, Z.-C., and Li, F.-M ((2000). Morphological Behavior for Micelle from Polystyrene-b-poly[2-β-d-glucopyranosyloxy)Ethyl Acrylate] upon Changing the Copolymer Concentration. Chem. Lett. 29(4),320-321.
79. You, L.-C., Lu, F.-Z., Li, Z.-C., Zhang, W., and Li, F.-M ((2002). Glucose-Sensitive Aggregates Formed by Poly(Ethylene Oxide)-Block-Poly(2-Glucosyl-Oxyethyl Acrylate) with Concanavalin A in Dilute Aqueous Medium. Macromolecules 36(1),1-4.
80. Narain, R., and Armes, S. P ((2002). Synthesis of Low Polydispersity, Controlled-Structure Sugar Methacrylate Polymers UnderMild Conditions without ProtectingGroup Chemistry. Chem. Commun. (23), 2776-2777.
81. Narain, R., and Armes, S. P. (2003). Direct Synthesis and Aqueous Solution Properties of Well-Defined Cyclic Sugar Methacrylate Polymers. Macromolecules 36(13),4675-4678.
82. Narain, R., and Armes, S. P ((2003). Synthesis and Aqueous Solution Properties of Novel Sugar Methacrylate-Based Homopolymers and Block Copolymers. Biomacromolecules 4(6),1746-1758.
83. Wang, X. S., and Armes, S. P ((2000). Facile Atom Transfer Radical Polymerization of Methoxy-Capped Oligo(Ethylene Glycol) Methacrylate in Aqueous Media at Ambient Temperature. Macromolecules 33(18),6640-6647.
84. Matyjaszewski, K., and Xia, J ((2001). Atom Transfer Radical Polymerization. Chem. Rev. 101(9),2921-2990.
85. Kickelbick, G., Reinohl, U., Ertel, T. S., Weber, A., Bertagnolli, H., and Matyjaszewski, K ((2000). Extended X-ray Absorption Fine Structure Analysis of the Bipyridine Copper Complexes in Atom Transfer Radical Polymerization. Inorg. Chem. 40(1),6-8.
86. Chen, Y.-M., and Wulff, G ((2002). ABA and Star Amphiphilic Block Copolymers Composed of PolymethacrylateBearing aGalactose Fragment and Poly(ε-Caprolactone). Macromol. Rapid Commun. 23(1),59-63.
87. Meng, J.-Q., Du, F.-S., Liu, Y.-S., and Li, Z.-C ((2005). Atom Transfer Radical Polymerization of 6-O-Methacryloyl-1,2;3,4-di-O-Isopropylidene-d-Galactopyranose in Solution. J. Polym. Sci. Part A: Polym. Chem. 43(4),752-762.
88. Suriano, F., Coulembier, O., Deöee, P., and Dubois, P ((2008). Carbohydrate-Based Amphiphilic Diblock Copolymers: Synthesis, Characterization, and Aqueous Properties. J. Polym. Sci. Part A: Polym. Chem. 46(11),3662-3672.
89. Dong, C.-M., Faucher, K. M., and Chaikof, E. L ((2004). Synthesis and Properties of Biomimetic Poly(l-Glutamate)-b-Poly(2-Acryloyloxyethyllactoside)-b-Poly(l-Glutamate) Triblock Copolymers. J. Polym. Sci. Part A: Polym. Chem. 42(22), 5754-5765.
90. Dong, C.-M., Sun, X.-L., Faucher, K. M., Apkarian, R. P., and Chaikof, E. L. (2003). Synthesis and Characterization of Glycopolymer-Polypeptide Triblock Copolymers. Biomacromolecules 5(1),224-231.
91. Dai,X.H., andDong, C. M ((2008). Synthesis, Self-Assembly and Recognition Properties of Biomimetic Star-Shaped Poly(ε-Caprolactone)-b-Glycopolymer Block Copolymers. J. Polym. Sci. Part A: Polym. Chem. 46(3),817-829.
92. Zhou, W., Dai, X.-H., and Dong, C.-M ((2008). Biodegradable and Biomimetic Poly(ε-Caprolactone)/Poly(Lactobionamidoethyl Methacrylate) Biohybrids: Synthesis, Lactose-Installed Nanoparticles and Recognition Properties. Macromol. Biosci. 8(3),268-278.
93. Qiu, S., Huang, H., Dai, X. H., Zhou,W., and Dong, C. M ((2009). Star-Shaped Polypeptide/ Glycopolymer Biohybrids: Synthesis, Self-Assembly, Biomolecular Recognition, and Controlled Drug Release Behavior. J. Polym. Sci. Part A: Polym. Chem. 47(8),2009-2023.
94. Dai, X.-H., Zhang, H.-D., and Dong, C.-M ((2009). Fabrication, Biomolecular Binding, in Vitro Drug Release Behavior of Sugar-Installed Nanoparticles from Star Poly(ε-Caprolactone)/Glycopolymer Biohybrid with a Dendrimer Core. Polymer 50(19),4626-4634.
95. Dai, X.-H., Dong, C.-M., and Yan, D ((2008). Supramolecular and Biomimetic Polypseudorotaxane/ Glycopolymer Biohybrids: Synthesis, Glucose-Surfaced Nanoparticles, and Recognition with Lectin. J. Phys. Chem. B 112(12),3644-3652.
96. Muthukrishnan, S., Zhang, M., Burkhardt, M., Drechsler,M., Mori, H., andMuller, A. H. E ((2005). Molecular Sugar Sticks: Cylindrical Glycopolymer Brushes. Macromolecules 38(19),7926-7934.
97. Muthukrishnan, S., Mori, H., and Muller, A. H. E ((2005). Synthesis and Characterization of Methacrylate-Type Hyperbranched Glycopolymers via Self-Condensing Atom Transfer Radical Copolymerization. Macromolecules 38(8),3108-3119.
98. Muthukrishnan, S., Plamper, F., Mori, H., and Muller, A. H. E ((2005). Synthesis and Characterization of Glycomethacrylate Hybrid Stars from Silsesquioxane Nanoparticles. Macromolecules 38(26),10631-10642.
99. Wang, J., Qian, Y., Zhang, F., Zhu, B., and Xu, Y ((2008). Synthesis and Self-Assembly of Amphiphilic ABA Type Triblock Copolymer with Well-Defined Glycopolymer Segments. Chin. Sci. Bull. 53(9),1343-1351.
100. Muthukrishnan, S., Jutz, G., Andre, X., Mori, H., and Muller, A. H. E ((2004). Synthesis of Hyperbranched Glycopolymers via Self-Condensing Atom Transfer Radical Copolymerization of a Sugar-Carrying Acrylate. Macromolecules 38(1),9-18.
101. Muthukrishnan, S., Nitschke, M., Gramm, S., Oz̈yörek, Z., Voit, B., Werner, C., and Müller, A. H. E ((2006). Immobilized Hyperbranched Glycoacrylate Films as Bioactive Supports. Macromol. Biosci. 6(8),658-666.
102. Muthukrishnan, S., Erhard, D. P., Mori, H., and Muller, A. H. E ((2006). Synthesis and Characterization of Surface-Grafted Hyperbranched Glycomethacrylates. Macromolecules 39(8),2743-2750.
103. Ejaz, M., Ohno, K., Tsujii, Y., and Fukuda, T ((2000). Controlled Grafting of a Well-Defined Glycopolymer on a Solid Surface by Surface-Initiated Atom Transfer Radical Polymerization. Macromolecules 33(8),2870-2874.
104. Gao, C., Muthukrishnan, S., Li, W., Yuan, J., Xu, Y., and Muller, A. H. E ((2007). Linear and Hyperbranched Glycopolymer-Functionalized Carbon Nanotubes: Synthesis, Kinetics, and Characterization. Macromolecules 40(6),1803-1815.
105. Yang, Q., Tian, J., Hu, M.-X., and Xu, Z.-K ((2007). Construction of a Comb-like Glycosylated Membrane Surface by a Combination of UV-Induced Graft Polymerization and Surface-Initiated ATRP. Langmuir 23(12),6684-6690.
106. Mateescu, A., Ye, J., Narain, R., and Vamvakaki, M ((2009). Synthesis and Characterization of Novel Glycosurfaces by ATRP. Soft Matter 5(8),1621-1629.
107. Raynor, J. E., Petrie, T. A., Fears, K. P., Latour, R. A., Garcia, A. J., and Collard, D. M ((2009). Saccharide Polymer Brushes to Control Protein and Cell Adhesion to Titanium. Biomacromolecules 10(4),748-755.
108. Gupta, S. S., Raja, K. S., Kaltgrad, E., Strable, E., and Finn, M. G ((2005). Virus-Glycopolymer Conjugates by Copper(I) Catalysis of Atom Transfer Radical Polymerization and Azide-Alkyne Cycloaddition. Chem. Commun. (34), 4315-4317.
109. Ladmiral, V., Monaghan, L., Mantovani, G., and Haddleton, D. M ((2005). α-Functional Glycopolymers: New Materials for (Poly)Peptide Conjugation. Polymer 46(19),8536-8545.
110. Lu, F.-Z.,Meng, J.-Q., Du, F.-S., Li, Z.-C., and Zhang, B.-Y ((2005). Pyrene End-Labeled Diblock Glycopolymers: Synthesis and Aggregation. Macromol. Chem. Phys. 206(4),513-520.
111. öazquez-Dorbatt, V., and Maynard, H. D ((2006). Biotinylated Glycopolymers Synthesized by Atom Transfer Radical Polymerization. Biomacromolecules 7(8),2297-2302.
112. Narain, R ((2006). Tailor-Made Protein-Glycopolymer Bioconjugates. React. Funct. Polym. 66(12),1589-1595.
113. Broyer, R. M., Quaker, G. M., and Maynard, H. D ((2007). Designed Amino Acid ATRP Initiators for the Synthesis of Biohybrid Materials. J. Am. Chem. Soc. 130(3),1041-1047.
114. Vázquez-Dorbatt, V., Tolstyka, Z. P., Chang, C.-W., and Maynard, H. D ((2009). Synthesis of a Pyridyl Disulfide End-Functionalized Glycopolymer for Conjugation to Biomolecules and Patterning on Gold Surfaces. Biomacromolecules 10(8),2207-2212.
115. Kitano, H., Takahashi, Y., Mizukami, K., and Matsuura, K ((2009). Kinetic Study on the Binding of Lectin to Mannose Residues in a Polymer Brush. Colloids and Surfaces B:Biointerfaces 70(1), 91-97.
116. Mizukami, K., Takakura, H., Matsunaga, T., and Kitano, H ((2008). Binding of Ricinus Communis Agglutinin to a Galactose-Carrying Polymer Brush on a Colloidal Gold Monolayer. Colloids Surf. B: Biointerf. 66 (1), 110-118.
117. Chiefari, J., Chong, Y. K., Ercole, F., Krstina, J., Jeffery, J., Le, T. P. T., Mayadunne, R. T. A.,Meijs,G. F., Moad,C. L., Moad,G., Rizzardo, E., and Thang, S. H ((1998). Living Free-Radical Polymerization by Reversible Addition-Fragmentation Chain Transfer:The RAFT Process. Macromolecules 31 (16), 5559-5562.
118. Corpart, P., Charmot, D., Zard, S., Franck, X., and Bouhadir, G ((1999). Method for Block Copolymer Synthesis by Controlled Radical Polymerisation fromDithiocarbamate Compounds. WO 99/35177.
119. Barner-Kowollik, C ((2008). Handbook of RAFT Polymerization. Wiley-VCH, Weinheim.
120. Lowe,A. B., Sumerlin, B. S., andMcCormick, C. L ((2003). The Direct Polymerization of 2-Methacryloxyethyl Glucoside via Aqueous Reversible Addition-Fragmentation Chain Transfer (RAFT) Polymerization. Polymer 44(22),6761-6765.
121. Albertin, L., Stenzel, M. H., Barner-Kowollik, C., Foster, L. J. R., and Davis, T. P ((2005). Well-Defined Diblock Glycopolymers from RAFT Polymerization in Homogeneous Aqueous Medium. Macromolecules 38(22),9075-9084.
122. Albertin, L., Stenzel, M. H., Barner-Kowollik, C., and Davis, T. P ((2006). Effect of an Added Base on (4-Cyanopentanoic Acid)-4-Dithiobenzoate Mediated RAFT Polymerization in Water. Polymer 47(4),1011-1019.
123. Albertin, L., Stenzel, M., Barner-Kowollik, C., Foster, L. J. R., and Davis, T. P ((2004). Well-Defined Glycopolymers from RAFT Polymerization: Poly(Methyl 6-OMethacryloyl-α-d-Glucoside) and Its Block Copolymer with 2-Hydroxyethyl Methacrylate. Macromolecules 37(20),7530-7537.
124. Vana, P., Davis, T. P., and Barner-Kowollik, C ((2002). Kinetic Analysis of Reversible Addition Fragmentation Chain Transfer (RAFT) Polymerizations: Conditions for Inhibition, Retardation, and Optimum Living Polymerization. Macromol. Theory Simul. 11(8),823-835.
125. Granville, A. M., Quémener, D., Davis, T. P., Barner-Kowollik, C., and Stenzel, M. H ((2007). Chemo-enzymatic Synthesis and RAFT Polymerization of 6-O-Methacryloyl Mannose: A Suitable Glycopolymer for Binding to the Tetrameric Lectin Concanavalin A? Macromol. Symp. 255(1),81-89.
126. Albertin, L., and Cameron, N. R ((2007). RAFT Polymerization of Methyl 6-OMethacryloyl-α-d-Glucoside in Homogeneous Aqueous Medium. A Detailed Kinetic Study at the Low Molecular Weight Limit of the Process. Macromolecules 40(17),6082-6093.
127. Albertin, L., Kohlert, C., Stenzel, M., Foster, L. J. R., and Davis, T. P ((2004). Chemoenzymatic Synthesis of Narrow-Polydispersity Glycopolymers: Poly(6-O-Vinyladipoyl-d-Glucopyranose). Biomacromolecules 5(2),255-260.
128. Lowe, A. B., and Wang, R ((2007). Synthesis of Controlled-Structure AB Diblock Copolymers of 3-O-Methacryloyl-1,2:3,4-di-O-Isopropylidene-d-Galactopyranose and 2-(Dimethylamino)Ethyl Methacrylate. Polymer 48(8),2221-2230.
129. McLeary, J. B., Tonge, M. P., and Klumperman, B ((2006). A Mechanistic Interpretation of Initialization Processes in RAFT-Mediated Polymerization. Macromol. Rapid Commun. 27(15),1233-1240.
130. Plummer, R., Goh, Y.-K., Whittaker, A. K., and Monteiro, M. J ((2005). Effect of Impurities in Cumyl Dithiobenzoate on RAFT-Mediated Polymerizations. Macromolecules 38(12),5352-5355.
131. özyörek, Z., Komber, H., Gramm, S., Schmaljohann, D., Mul̈ler, A. H. E., and Voit, B ((2007). Thermoresponsive Glycopolymers via Controlled Radical Polymerization. Macromol. Chem. Phys. 208(10),1035-1049.
132. Al-Bagoury, M., Buchholz, K., and Yaacoub, E.-J ((2007). Synthesis of Well-Designed Polymers Carrying SaccharideMoieties via RAFT Miniemulsion Polymerization. Polym. Adv. Technol. 18(4),313-322.
133. Wang, J., Zhu, X.,Cheng, Z., Zhang, Z., and Zhu, J ((2007). Preparation, Characterization, and Chiral Recognition of Optically Active Polymers Containing Pendent Chiral Units via Reversible Addition-Fragmentation Chain Transfer Polymerization. J. Polym. Sci. Part A: Polym. Chem. 45(16),3788-3797.
134. Bernard, J., Favier, A., Zhang, L., Nilasaroya, A., Davis, T. P., Barner-Kowollik, C., and Stenzel, M. H ((2005). Poly(Vinyl Ester) Star Polymers via Xanthate-Mediated Living Radical Polymerization: from Poly(Vinyl Alcohol) to Glycopolymer Stars. Macromolecules 38(13),5475-5484.
135. Bernard, J., Hao, X., Davis, T. P., Barner-Kowollik, C., and Stenzel, M. H ((2005). Synthesis of Various Glycopolymer Architectures via Raft Polymerization: From Block Copolymers to Stars. Biomacromolecules 7(1),232-238.
136. Zhang, L., and Stenzel, M. H ((2009). Spherical Glycopolymer Architectures Using RAFT: From Stars with a β-Cyclodextrin Core to Thermoresponsive Core-Shell Particles. Aust. J. Chem. 62(8),813-822.
137. Cameron, N. R., Spain, S. G., Kingham, J. A., Weck, S., Albertin, L., Barker, C. L., Battaglia, G., Smart, T., and Blanazs, A ((2007). Synthesis of Well-Defined Glycopolymers and Some Studies of Their Aqueous Solution Behaviour. Faraday Discuss. 139, 359-368.
138. Pearson, S.,Allen, N., and Stenzel, M. H ((2009).Core-Shell Particleswith Glycopolymer Shell and Polynucleoside Core via RAFT: From Micelles to Rods. J. Polym. Sci. Part A:Polym. Chem. 47(6),1706-1723.
139. Ramiah, V., Matahwa, H.,Weber,W., McLeary, J. B., and Sanderson, R. D ((2007). CMC and Phase Separation Studies of RAFT Mediated Amphiphilic Diblock Glycopolymers with Methyl Acrylate and Styrene. Macromol. Symp. 255(1),70-80.
140. Pasparakis, G., and Alexander, C ((2008). Sweet Talking Double Hydrophilic Block Copolymer Vesicles. Angew. Chem. Int. Ed. 47(26),4847-4850.
141. Ting, S. R. S., Granville, A. M., Quemener, D., Davis, T. P., Stenzel, M. H., and Barner-Kowollik, C ((2007). RAFT Chemistry and Huisgen 1,3-Dipolar Cycloaddition: A Route to Block Copolymers of Vinyl Acetate and 6-O-Methacryloyl Mannose? Aust. J. Chem. 60(6),405-409.
142. Xiao, N.-Y., Li, A.-L., Liang, H., and Lu, J ((2008). A Well-Defined Novel Aldehyde-Functionalized Glycopolymer: Synthesis, Micelle Formation, and Its Protein Immobilization. Macromolecules 41(7),2374-2380.
143. Zhang, L., Bernard, J., Davis, T. P., Barner-Kowollik, C., and Stenzel, M. H ((2008). Acid-Degradable Core-CrosslinkedMicelles Prepared from Thermosensitive Glycopolymers Synthesized via RAFT Polymerization. Macromol. Rapid Commun. 29(2),123-129.
144. Ting, S. R. S., Gregory, A. M., and Stenzel, M. H ((2009). Polygalactose Containing Nanocages: The RAFT Process for the Synthesis of Hollow Sugar Balls. Biomacromolecules 10(2),342-352.
145. Stenzel, M. H., Zhang, L., and Huck, W. T. S ((2006). Temperature-Responsive Glycopolymer Brushes Synthesized via RAFT PolymerizationUsing the Z-Group Approach. Macromol. Rapid Commun. 27(14),1121-1126.
146. Guo, T.-Y., Liu, P., Zhu, J.-W., Song, M.-D., and Zhang, B.-H ((2006). Well-Defined Lactose-Containing Polymer Grafted onto Silica Particles. Biomacromolecules 7(4),1196-1202.
147. Spain, S. G., Albertin, L., and Cameron, N. R ((2006). Facile in Situ Preparation of Biologically Active Multivalent Glyconanoparticles. Chem. Commun. 4198-4200.
148. Gibson, M. I., Barker, C. A., Spain, S. G., Albertin, L., and Cameron, N. R ((2008). Inhibition of Ice Crystal Growth by Synthetic Glycopolymers: Implications for the Rational Design of Antifreeze Glycoprotein Mimics. Biomacromolecules 10(2),328-333.
149. Housni, A., Cai, H., Liu, S., Pun, S. H., and Narain, R ((2007). Facile Preparation of Glyconanoparticles and Their Bioconjugation to Streptavidin. Langmuir 23(9),5056-5061.
150. Narain, R., Housni, A., Gody, G., Boullanger, P., Charreyre, M.-T., and Delair, T ((2007). Preparation of Biotinylated Glyconanoparticles via a Photochemical Process and Study of Their Bioconjugation to Streptavidin. Langmuir 23(26),12835-12841.
151. Gody, G., Boullanger, P., Ladaviere, C., Charreyre, M.-T., andDelair, T ((2008). Biotin α-End-Functionalized Gradient Glycopolymers Synthesized by RAFT Copolymerization. Macromol. Rapid Commun. 29(6),511-519.
152. Toyoshima, M., and Miura, Y ((2009). Preparation of Glycopolymer-Substituted Gold Nanoparticles and Their Molecular Recognition. J. Polym. Sci. Part A: Polym. Chem. 47(5),1412-1421.
153. Kitano, H., Hayashi, A., Takakura, H., Suzuki, H., Kanayama, N., and Saruwatari, Y ((2009). Anti-biofouling Properties of a Telomer Brush with Pendent Glucosylurea Groups. Langmuir 25(16),9361-9368.
154. Deng, Z. C., Li, S. Q., Jiang, X. Z., and Narain, R ((2009). Well-Defined Galactose-Containing Multi-Functional Copolymers and Glyconanoparticles for Biomolecular Recognition Processes. Macromolecules 42(17),6393-6405.
155. Deng, Z. C.,Ahmed, M., and Narain, R ((2009).NovelWell-Defined Glycopolymers Synthesized via the Reversible Addition Fragmentation Chain Transfer Process in Aqueous Media. J. Polym. Sci. Part A: Polym. Chem. 47(2),614-627.
156. Ahmed, M., Jiang, X., Deng, Z., and Narain, R ((2009). Cationic Glyco-Functionalized Single-Walled Carbon Nanotubes as Efficient Gene Delivery Vehicles. Bioconjug. Chem. 20(11),2017-2022.
157. Jiang, X., Ahmed, M., Deng, Z., and Narain, R ((2009). Biotinylated Glyco-Functionalized Quantum Dots: Synthesis, Characterization, and Cytotoxicity Studies. Bioconjug. Chem. 20(5),994-1001.
158. Odian, G ((2005). Principles of Polymerization, 4th ed. Hoboken, NJ:Wiley-Interscience, pp. 619-744.
159. Good, F. J., and Schuerch, C ((1985). Synthesis of (1-3)-α-d-Glucopyranan by Stereoregular Cationic Polymerization of Substituted 2,6-Dioxabicyclo[3.1.1]Heptanes:1,3-Anhydrotri(p-Substituted-Benzyl)-β-d-Glucopyranoses. Macromolecules 18(4),595-599.
160. Uryu, T., Yamaguchi, C., Morikawa, K., Terui, K., Kanai, T., and Matsuzaki, K ((1985). Ring-Opening Polymerization of 1,4-Anhydro-2,3,6-tri-O-Benzyl-α-d-Glucopyranoseand 1,4-Anhydro-2,3,6-tri-O-Benzyl-β-d-Galactopyranose. Macromolecules 18(4),599-605.
161. Rude, E., Westphal, O., Hurwitz, E., Fuchs, S., and Sela, M ((1966). Synthesis and Antigenic Properties of Sugar-PolypeptideConjugates. Immunochemistry 3(2),137-151.
162. Okada, M., Aoi, K., and Tsutsumiuchi, K ((1997). Synthesis of Glycopeptide-Conjugates via Ring-Opening Polymerization of Sugar-Substituted Alpha-Amino Acid N-Carboxyanhydrides (GlycoNCAs). Proc. Jpn. Acad. Series B, Phys. Biol. Sci. 73(10),205-209.
163. Aoi, K., Tsutsumiuchi, K., and Okada, M ((1994). Glycopeptide Synthesis by an α-Amino Acid N-Carboxyanhydride (NCA) Method: Ring-Opening Polymerization of a Sugar-Substituted NCA. Macromolecules 27(3),875-877.
164. Tsutsumiuchi, K., Aoi, K., and Okada, M ((1997). Synthesis of Polyoxazoline-(glyco)Peptide Block Copolymers by Ring-Opening Polymerization of (Sugar-Substituted) Alpha-Amino Acid N-Carboxyanhydrides with Polyoxazoline Macroinitiators. Macromolecules 30(14),4013-4017.
165. Tsutsumiuchi, K., Aoi, K., and Okada, M ((1995). Synthesis of Novel Glycopeptide-Polyoxazoline Block-Copolymers by Direct Coupling between Living Anionic and Cationic Polymerization Systems. Macromol. Rapid Commun. 16(10),749-755.
166. Aoi, K., Suzuki, H., and Okada, M ((1992). Architectural Control of Sugar-Containing Polymers by Living Polymerization: Ring-Opening Polymerization of 2-Oxazolines Initiated with Carbohydrate Derivatives. Macromolecules 25(25),7073-7075.
167. Aoi, K., Tsutsumiuchi, K., Aoki, E., and Okada,M ((1996). First Synthesis of Glycopeptide Macromonomers and Graft-Type Sugar-Containing Polymers with Glycopeptide Side Chains. Macromolecules 29(12),4456-4458.
168. Odian, G ((2005). Principles of Polymerization, 4th ed. Hoboken, NJ:Wiley-Interscience, pp. 372-463.
169. Loykulnant, S., Hayashi, M., and Hirao, A ((1998). Protection and Polymerization of Functional Monomers. 28. Anionic Living Polymerization of Styrene Derivatives Containing Acetal-Protected Monosaccharide Residues. Macromolecules 31(26),9121-9126.
170. Loykulnant, S., and Hirao, A ((2000). Protection and Polymerization of Functional Monomers. 30. Anionic Living Polymerization of 4-Alkylstyrenes Containing Acetal-Protected Monosaccharide Residues. Macromolecules 33(13),4757-4764.
171. Minoda,M.,Yamaoka,K.,Yamada,K., Takaragi,A., andMiyamoto, T ((1995). Synthesis of Functional Polymers Bearing Pendant Monosaccharide and Oligosaccharide Residues. Macromol. Symp. 99, 169-177.
172. Yamada, K., Minoda, M., and Miyamoto, T ((1997). Controlled Synthesis of Glycopolymers with Pendant d-Glucosamine Residues by LivingCationic Polymerization. J. Polym. Sci. Part A: Polym. Chem. 35(4),751-757.
173. Yamada, K., Yamaoka, K., Minoda, M., and Miyamoto, T ((1997). Controlled Synthesis of Amphiphilic Block Copolymers with Pendant Glucose Residues by Living Cationic Polymerization. J. Polym. Sci. Part A: Polym. Chem. 35(2),255-261.
174. Yamada, K., Minoda, M., and Miyamoto, T ((1999). Controlled Synthesis of Amphiphilic Block Copolymers with Pendant N-Acetyl-d-Glucosamine Residues by Living Cationic Polymerization and Their Interaction with WGA Lectin. Macromolecules 32(11),3553-3558.
175. Yamada, K., Minoda, M., Fukuda, T., and Miyamoto, T ((2001). Amphiphilic Block and Statistical Copolymers with Pendant Glucose Residues: Controlled Synthesis by Living Cationic Polymerization and the Effect of Copolymer Architecture on Their Properties. J. Polym. Sci. Part A: Polym. Chem. 39(4),459-467.
176. Labeau, M. P., Cramail, H., and Deffieux, A ((1998). Amphiphilic Block Copolymers of Controlled Dimensions with Hydrophilic Glycosidic Vinyl Ether Moieties. Macromol. Chem. Phys. 199(3),335-342.
177. D'Agosto, F., Charreyre, M. T., Pichot, C., and Mandrand, B ((2002). Polymer of Controlled Chain Length Carrying Hydrophilic Galactose Moieties for Immobilization of DNA Probes. Macromol. Chem. Phys. 203(1), 146-154.
178. 'Agosto, F., Charreyre, M. T., Delolme, F., Dessalces, G., Cramail, H., Deffieux, A., and Pichot, C ((2002). Kinetic Study of the "Living" Cationic Polymerization of a Galactose Carrying Vinyl Ether. MALDI-TOF MS Analysis of the Resulting Glycopolymers. Macromolecules 35(21),7911-7918.
179. Odian, G ((2005). Principles of Polymerization, 4th ed. Hoboken, NJ:Wiley-Interscience, pp. 590-592.
180. Mortell, K. H., Gingras,M., and Kiessling, L. L ((1994). Synthesis of Cell Agglutination Inhibitors by Aqueous Ring-Opening Metathesis Polymerization. J. Am. Chem. Soc. 116(26),12053-12054.
181. Mortell, K. H.,Weatherman, R.V., and Kiessling, L. L ((1996). Recognition Specificity of Neoglycopolymers Prepared by Ring-OpeningMetathesis Polymerization. J. Am. Chem. Soc. 118(9),2297-2298.
182. Schuster, M. C., Mortell, K. H., Hegeman, A. D., and Kiessling, L. L ((1997). Neoglycopolymers Produced by Aqueous Ring-OpeningMetathesis Polymerization: Decreasing Saccharide Density Increases Activity. J. Mol. Catal. A: Chem. 116(1-2), 209-216.
183. Manning, D. D., Hu, X., Beck, P., and Kiessling, L. L ((1997). Synthesis of Sulfated Neoglycopolymers: Selective P-Selectin Inhibitors. J. Am. Chem. Soc. 119(13),3161-3162.
184. Sanders,W. J., Gordon, E. J., Dwir, O., Beck, P. J., Alon, R., and Kiessling, L. L ((1999). Inhibition of L-Selectin-Mediated Leukocyte Rolling by Synthetic GlycoproteinMimics. J. Biol. Chem. 274(9),5271-5278.
185. Fraser, C., and Grubbs, R. H ((1995). Synthesis of Glycopolymers of Controlled Molecular-Weight by Ring-Opening Metathesis Polymerization Using Well-Defined Functional-Group Tolerant Ruthenium Carbene Catalysts. Macromolecules 28(21),7248-7255.
186. Kanai, M., Mortell, K. H., and Kiessling, L. L ((1997). Varying the Size of Multivalent Ligands: The Dependence of Concanavalin a Binding on Neoglycopolymer Length. J. Am. Chem. Soc. 119(41),9931-9932.
187. Nomura, K., and Schrock, R. R ((1996). Preparation of 'Sugar-Coated' Homopolymers and Multiblock ROMP Copolymers. Macromolecules 29(2),540-545.
188. Martínez, G., Fernández-García, M., and Sánchez-Chaves, M ((2005). Synthesis and Characterization of N-Vinylpyrrolidone-tert-Butyl Methacrylate-Methacrylic Acid Terpolymers Having Amino Sugar or Bioactive Amino Side Compounds. J. Polym. Sci. Part A: Polym. Chem. 43(1),18-27.
189. Sánchez-Chaves, M.,Arranz, F., and Cortazar, M ((1998). Poly (VinylAlcohol) Functionalized by Monosuccinate Groups. Coupling of Bioactive Amino Compounds. Polymer 39(13),2751-2757.
190. Bahulekar, R., Tokiwa, T., Kano, J., Matsumura, T., Kojima, I., and Kodama, M ((1998). Polyacrylamide Containing Sugar Residues: Synthesis, Characterization and Cell Compatibility Studies. Carbohydr. Polym. 37(1),71-78.
191. Strong, L. E., and Kiessling, L. L ((1999). A General Synthetic Route to Defined, Biologically Active Multivalent Arrays. J. Am. Chem. Soc. 121(26),6193-6196.
192. Baek, M.-G., and Roy, R ((2001). Relative Lectin Binding Properties of TAntigen-Containing Glycopolymers: Copolymerization of N-Acryloylated T-Antigen Monomer vs. Graft Conjugation of Aminated T-Antigen Ligands onto Poly(NAcryloxysuccinimide). Macromol. Biosci. 1(7),305-311.
193. Hu, Z., Liu, Y., Hong, C., and Pan, C ((2005). Synthesis ofWell-Defined Glycoconjugate Polyacrylamides via Preactivated Polymers Prepared byATRP. J, Appl. Polym. Sci. 98(1),189-194.
194. Auzely-Velty, R., Cristea, M., and Rinaudo, M ((2002). Galactosylated NVinylpyrrolidone-Maleic Acid Copolymers: Synthesis, Characterization, and Interaction with Lectins. Biomacromolecules 3(5),998-1005.
195. García-Oteiza, M. C., Sánchez-Chaves, M., and Arranz, F ((1997). Poly(Vinyl Alcohol) Having Amino Sugar as the Pendant Group: Synthesis, Characterization and Binding of Concanavalin A. Macromol. Chem. Phys. 198(7),2237-2247.
196. Cerrada,M. L., Sönchez-Chaves, M., Ruiz, C., and Fernöndez-Garciö, M ((2009). Recognition Abilities and Development of Heat-Induced Entangled Networks in Lactone-Derived Glycopolymers Obtained from Ethylene-Vinyl Alcohol Copolymers. Biomacromol. 10(7),1828-1837.
197. Ladmiral, V., Mantovani, G., Clarkson, G. J., Cauet, S., Irwin, J. L., and Haddleton, D. M ((2006). Synthesis of Neoglycopolymers by a Combination of "Click Chemistry" and Living Radical Polymerization. J. Am. Chem. Soc. 128(14), 4823-4830.
198. Chen, G., Tao, L., Mantovani, G., Geng, J., Nystroem, D., and Haddleton, D. M ((2007). A Modular Click Approach to Glycosylated Polymeric Beads: Design, Synthesis and Preliminary Lectin Recognition Studies. Macromolecules 40(21), 7513-7520.
199. Geng, J., Mantovani, G., Tao, L., Nicolas, J., Chen, G., Wallis, R., Mitchell, D. A., Johnson, B. R. G., Evans, S. D., and Haddleton, D. M ((2007). Site-Directed Conjugation of "Clicked" Glycopolymers to form Glycoprotein Mimics: Binding to Mammalian Lectin and Induction of Immunological Function. J. Am. Chem. Soc. 129(49),15156-15163.
200. Geng, J., Lindqvist, J., Mantovani, G., Chen, G., Sayers, C. T., Clarkson, G. J., and Haddleton, D. M ((2007). Well-Defined Poly(N-Glycosyl 1,2,3-Triazole) Multivalent Ligands: Design, Synthesis and Lectin Binding Studies. QSAR Combin. Sci. 26(11-12), 1220-1228.
201. Nurmi, L., Lindqvist, J., Randev, R., Syrett, J., and Haddleton, D. M. (2009). Glycopolymers via Catalytic Chain Transfer Polymerisation (CCTP), Huisgens Cycloaddition and Thiol-EneDoubleClickReactions. Chem.Commun. (19), 2727-2729.
202. Chen, G., Amajjahe, S., and Stenzel, M. H ((2009). Synthesis of Thiol-Linked Neoglycopolymers and Thermo-Responsive Glycomicelles as Potential Drug Carrier. Chem. Commun. (10), 1198-1200.
203. You, L., and Schlaad, H ((2006). An Easy Way to Sugar-Containing Polymer Vesicles or Glycosomes. J. Am. Chem. Soc. 128(41),13336-13337.
204. Diehl, C., and Schlaad, H ((2009). Thermo-Responsive Polyoxazolines with Widely Tuneable LCST. Macromol. Biosci. 9(2),157-161.
205. Takasu,A., Niwa, T., Itou, H., Inai,Y., and Hirabayashi, T ((2000). Chemical Modification of Hydroxyl Groups of Poly(Vinyl Alcohol) by a Glycosidation Reaction. Macromol. Rapid Commun. 21(11),764-769.
206. Xue, C., Donuru, V. R. R., and Liu, H ((2006). Facile, Versatile Prepolymerization and Postpolymerization Functionalization Approaches for Well-Defined Fluorescent Conjugated Fluorene-Based Glycopolymers. Macromolecules 39(17),5747-5752.
207. Zhu, J., Gosen, C., and Marchant, R. E ((2006). Synthesis and Characterization of Poly(Vinyl Amine)-Based Amphiphilic Comb-like Dextran Glycopolymers by a Two-Step Method. J. Polym. Sci. Part A: Polym. Chem. 44(1),192-199.
208. Renaudie, L., Le Narvor, C., Lepleux, E., and Roger, P ((2007). Functionalization of Poly(ethylene terephthalate) Fibers by Photografting of a Carbohydrate Derivatized with a Phenyl Azide Group. Biomacromolecules 8(2),679-685.