Abstract
Polysaccharides having various contents of carboxyl group precursors were synthesized by ring-opening copolymerization of 1,6-anhydro-2,4-di-O-benzyl-3-O-1-(methoxycarbonyl)ethyl-β-D-glucopyranose (1) with tri-O-benzyl-levoglucosan (2) with phosphorus pentafluoride as catalyst in methylene chloride at −60°C. The monomer reactivity ratios calculated by Kelen–Tüdös method were r1=0.77 and r2=0.71. Birch reduction with lithium metal was quite effective for the deprotection of both methyl ester and benzyl ether groups of the polymer.
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References
I. Björk and U. Lindahl, Mol. Cell. Biochem., 48, 161 (1982).
M.-C. Bourin and U. Lindahl, Biochem. J., 289, 313 (1993).
M. Baba, R. Pauwels, J. Balzarini, J. Arnout, J. Desmyter, and E. de Clercq, Proc. Natl. Acad. Sci. U.S.A., 85, 6132 (1988).
R. L. Jackson, S. J. Busch, and A. D. Cardin, Physiol. Rev., 71, 481 (1991).
M. Sorm, S. Nespurek, L. Mrkvicková, J. Kálal, and Z. Vorlová, J. Polym. Sci., Polym. Symp., 66, 349 (1979).
J. Hoffman, O. Larm, K. Larsson, L.O. Andersson, E. Holmer, and G. Söderström, Carbohydr. Polym., 2, 115 (1982).
M. Mauzac and J. Jozefonvicz, Biomaterials, 5, 301 (1984).
K. Hatanaka, T. Yoshida, S. Miyahara, T. Sato, F. Ono, T. Uryu, and H. Kuzuhara, J. Med. Chem., 30, 810 (1987).
K. Hatanaka, Y. Kurihara, T. Uryu, O. Yoshida, N. Yamamoto, T. Mimura, and Y. Kaneko, Carbohydr. Res., 214, 147 (1991).
V. Crescenzi, M. Dentini, and T. Coviello, Biophys. Chem., 41, 61 (1991).
M. Fujihara, N. Iizima, I. Yamamoto, and T. Nagumo, Carbohydr. Res., 125, 97 (1984).
M. Fujihara and T. Nagumo, Carbohydr. Res., 224, 343 (1992).
T. Heinze, D. Klemm, F. Loth, and B. Philipp, Acta Polym., 41, 259 (1990).
S.-I. Nishimura, N. Nishi, and S. Tokura, Carbohydr. Res., 146, 251 (1986).
K. Hatanaka, T. Uryu, S. Miyahara, and H. Kuzuhara, J. Polym. Sci., A: Polym. Chem., 30, 1223 (1992).
M. A. Zottola, R. Alonso, G. D. Vite, and B. Fraser-Reid, J. Org. Chem., 54, 6123 (1989).
T. Uryu, H. Tachikawa, K.-I. Ohaku, K. Terui, and K. Matsuzaki, Makromol. Chem., 178, 1929 (1977).
T. Kelen and F. Tüdös, J. Macromol. Sci., Chem., A9, 1 (1975).
J. P. Kennedy, T. Kelen, and F. Tüdös, J. Polym. Sci., Polym. Chem. Ed., 13, 2277 (1975).
S. A. Barker, E. J. Bourne, M. Stacey, and D. H. Whiffen, J. Chem. Soc., 171 (1954).
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Hatanaka, K., Minamisawa, T. & Kanno, KI. Syntheses of Polysaccharides Having Various Contents of Carboxyl Groups by Ring-Opening Copolymerization. Polym J 27, 1016–1020 (1995). https://doi.org/10.1295/polymj.27.1016
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DOI: https://doi.org/10.1295/polymj.27.1016
