Synthesis of a well-defined glycopolymer by nitroxide-controlled free radical polymerization

Macromolecules

Volumn 31, Issue 4, 1998, Pages 1064-1069

  Ohno, Kohji ^a   Tsujii, Yoshinobu ^a   Miyamoto, Takeaki ^a   Fukuda, Takeshi ^a   Goto, Mitsuaki ^b   Kobayashi, Kazukiyo ^c   Akaike, Toshihiro ^d  

^a KYOTO UNIVERSITY   (Japan)

^b Bioquest Co Ltd   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

^d TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERS; DERIVATIVES; FREE RADICAL POLYMERIZATION; INITIATORS (CHEMICAL); MOLECULAR DYNAMICS; MOLECULAR WEIGHT; NITROGEN OXIDES; POLYSACCHARIDES; POLYSTYRENES; REACTION KINETICS;

GLYCOPOLYMER; NITROXIDE CONTROLLED POLYMERIZATION; POLYDISPERSITY;

SYNTHESIS (CHEMICAL);

EID: 0031998512     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma971329g     Document Type: Article

References (57)

1. Fukuda, M., Hindsgaul, O., Eds. Molecular Glycobiology; Oxford University Press: New York, 1994.
2. (a) Lee, Y. C., Lee R. T., Eds. Neoglycoconjugates: Preparation and Applications; Academic Press: San Diego, CA, 1994.
3. (b) Lee, Y. C., Lee, R. T., Eds. Methods in Enzymology; Academic Press: San Diego, CA, 1994; Vol. 242.
4. (c) Lee, Y. C., Lee, R. T., Eds. Methods in Enzymology; Academic Press: San Diego, CA, Vol. 247.
5. Collins, P. M.; Ferner, R. J. Monosaccharides: Their Chemistry and Their Roles in Natural Products; John Wiley and Sons: Chichester, U.K., 1995.
6. Wulff, G.; Schmid, J.; Venhoff, T. Macromol. Chem. Phys. 1996, 197, 259 and references therein.
7. (a) Yamada, K.; Yamaoka, K.; Minoda, M.; Miyamoto, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 255.
8. (b) Yamada, K.; Minoda, M.; Miyamoto, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 751.
9. Fraser, C.; Grubbs, R. H. Macromolecules 1995, 28, 7248.
10. (a) Aoi, K.; Suzuki, H.; Okada, M. Macromolecules 1992, 25, 7073.
11. (b) Aoi, K.; Tsutsumiuchi, K.; Okada, M. Macromolecules 1994, 27, 875.
12. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
13. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
14. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
15. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
16. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
17. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
18. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
19. For recent reviews, see: (a) Moad, G.; Rizzardo, E.; Solomon, D. H. In Comprehensive Polymer Science; Eastmond, G. C., Ledwith, A., Russo, S., Sigwalt, P., Eds.: Pergamon: London, 1989; Vol. 3, p 141. (b) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Trends Polym. Sci. 1994, 2, 66. (c) Matyjaszewski, K.; Gaynor, S.; Greszta, D.; Mardare, D.; Shigemoto, T. J. Phys. Org. Chem. 1995, 8, 306. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, U.K., 1995; p 335. (e) Davis, T. P.; Haddleton, D. M. In New Methods of Polymer Synthesis; Ebdon, J. R., Eastmond, G. C., Eds.; Blackie: Glasgow, U.K., 1995; Vol. 2, p 1. (f) Hawker, C. J. Trends Polym. Sci. 1996, 4, 183. (g) Sawamoto, M.; Kamigaito, M. In Polymer Synthesis; Materials Science and Technology Series; VCH: Deerfield v Beach, FL (in press). (h) Fukuda, T.; Goto, A.; Ohno, K.; Tsujii, Y. In Advances in Free Radical Polymerization; Matyjaszewski, K., Ed.; American Chemical Society Washington, DC (in press).
20. (a) Solomon, D. H.; Rizzardo, E.; Cacioli, P. Eur. Pat. Appl. 135280, 1985; Chem. Abstr. 1985, 102, 221335q.
21. (b) Rizzardo, E. Chem. Aust. 1987, 54, 32.
22. (c) Johnson, C. H. J.; Moad, G.; Solomon, D. H.; Spurling, T. H.; Vearing, D. J. Aust. J. Chem. 1990, 43, 1215.
23. (d) Georges, M. K.; Veregin, R. P. N.; Kazmaier, P. M.; Hamer, G. K. Macromolecules 1993, 26, 2987.
24. (e) Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638.
25. (f) Hawker, C. J. J. Am. Chem. Soc. 1994, 116, 11185.
26. (g) Hawker, C. J.; Hedrick, J. L. Macromolecules 1995, 28, 2993.
27. (h) Catala, J. M.; Bubel, F.; Hammouch, S. O. Macromolecules 1995, 28, 8441.
28. (i) Fukuda, T.; Terauchi, T.; Goto, A.; Tsujii, Y.; Miyamoto, T.; Shimizu, Y. Macromolecules 1996, 29, 3050.
29. (j) Howell, B. A.; Priddy, D. B.; Li, I. Q.; Smith, P. B.; Kastl, P. E. Polym. Bull. 1996, 37, 451.
30. Hawker, C. J.; Elce, E.; Dao, J.; Volksen, W.; Russell, T. P.; Barclay, G. G. Macromolecules 1996, 29, 2686.
31. Ide, N.; Fukuda, T. Macromolecules 1997, 30, 4268.
32. Ohno, K.; Fukuda, T.; Miyamoto, T.; Shimizu, Y. Macromol. Chem. Phys., in press.
33. Hawker, C. J.; Mecerreyes, D.; Elce, E.; Dao, J.; Hedrick, J. L.; Barakat, L; Dubois, P.; Jérôme, R.; Volksen, W. Macromol. Chem. Phys. 1997, 198, 155.
34. Bon, S. A. F.; Bosveld, M.; Klumperman, B.; German, A. L. Macromolecules 1997, 30, 0, 324.
35. Keoshkerian, B.; Georges, M. K.; Boils-Boissier, D. Macromolecules 1995, 28, 6381.
36. Hawker, C. J.; Barclay, G. G.; Orellana, A.; Dao, J.; Devonport, W. Macromolecules 1996, 29, 5245.
37. (a) Fukuda, T.; Terauchi, T. Chem. Lett. (Tokyo) 1996, 293.
38. (b) Fukuda, T.; Terauchi, T.; Goto, A.; Ohno, K.; Tsujii, Y.; Miyamoto, T.; Kobatake, S.; Yamada, B. Macromolecules 1996, 29, 6393.
39. (c) Greszta, D.; Matyjaszewski, K. Macromolecules 1996, 29, 7661.
40. (d) Odell, P. G.; Veregin, R. P. N.; Michalak, L. M.; Georges, M. K. Macromolecules 1997, 30, 2232.
41. (a) Goto, A.; Fukuda, T. Macromolecules 1997, 30, 5183.
42. (b) Goto, A.; Terauchi, T.; Fukuda, T.; Miyamoto, T. Macromol. Rapid Commun. 1997, 18, 673.
43. (c) Goto, A.; Fukuda, T. Macromolecules 1997, 30, 4272.
44. (d) Fukuda, T.; Goto, A. Macromol. Rapid Commun. 1997, 18, 682.
45. Kobayashi, K.; Sumitomo, H.; Ina, Y. Polym J. 1985, 17, 567.
46. Fukuda, T.; Ma, Y.-D.; Inagaki, H. Macromolecules 1985, 18, 17.
47. Ma, Y.-D.; Fukuda, T.; Inagaki, H. Polym. J. (Tokyo) 1983, 15, 673.
48. Moad, G.; Rizzardo, E. Macromolecules 1995, 28, 8722.
49. Kazmaier, P. M.; Moffat, K. A.; Georges, M. K.; Veregin R. P. N.; Hamer, G. K. Macromolecules 1995, 28, 1841.
50. (a) Tsujii, Y.; et al. To be published.
51. (b) Tsujii, Y.; Fukuda, T.; Miyamoto, T. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1997, 38 (1), 657.
52. Fisher, H. Macromolecules 1997, 30, 5666.
53. (a) Li, I.; Howell, B. A.; Matyjaszewski, K.; Shigemoto, T.; Smith, P. B.; Priddy, D. B. Macromolecules 1995, 28, 6692.
54. (b) Ohno, K.; Tsujii, Y.; Fukuda, T. Macromolecules 1997, 30, 2503.
55. Greszta, D.; Matyjaszewski, K. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 1857.
56. Bailey, H. C.; Godin, G. W. Trans. Faraday Soc. 1956, 52, 68.
57. Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294.