Abstract
(1→6)-α-Linked heteropolysaccharides composed of D-glucose and 2,3,4-trideoxy-DL-glycero-hexopyranose units were synthesized by cationic ring-opening copolymerization of 1,6-anhydro-2,3,4-tri-O-beazyl-β-D-glucose (TBLG) with rac-4(e)-bromo-6,8-dioxabicyclo[3.2.1]octane (BrDBO) followed by reductive debromination and subsequent debenzylation. The heteropolysaccharides (mole fraction of D-glucose unit, 0.34–0.90) were soluble in water and dimethyl sulfoxide, and insoluble in other organic solvents. Hydrolysis of the hetero-polysaccharides by an endodextranase from a Penicillium species was examined in an acetate buffer solution (pH 5.3) at 37°C. The maximum degree of hydrolysis based on the D-glucose units, (D.H.)D, decreased significantly with increasing 2,3,4-trideoxy-DL-glycero-hexopyranose units. The observed (D.H.)D values were in agreement with those calculated from the diad fractions of the original TBLG-BrDBO copolymers by a statistical treatment previously proposed for the enzymatic hydrolysis of DL-dextran.
Similar content being viewed by others
Article PDF
References
E. J. Bourne, D. H. Hudson, and H. Weigel, Biochem. J., 85, 158 (1962).
J. Fukumoto, H. Tsuji, and D. Tsuru, J. Biochem., 69, 1113 (1971).
D. Tsuru, N. Hiraoka, and J. Fukumoto, J. Biochem., 71, 653 (1972).
G. J. Walker, Carbohydr. Res., 30, 1 (1973).
G. J. Walker and A. Pulkownik, Carbohyd. Res., 36, 53 (1974).
G. J. Walker and M. B. Dewar, Carbohydr. Res., 39, 303 (1975).
A. Pulkownik, J. A. Thoma, and G. J. Walker, Carbohydr. Res., 61, 493 (1978).
M. Okada, H. Sumitomo, T. Hirasawa, K. Ihara, and Y. Tada, Polym. J., 18, 601 (1986).
M. Okada, H. Sumitomo, and T. Hirasawa, Biopolymers, 25, 1955 (1986).
M. Okada, H. Sumitomo, and H. Komada, Makromol. Chem., 179, 949 (1978).
H. Komada, M. Okada, and H. Sumitomo, Makromol. Chem., 179, 2859 (1978).
M. Okada, H. Sumitomo, M. Hasegawa, and H. Komada, Makromol. Chem., 180, 813 (1979).
H. Komada, M. Okada, and H. Sumitomo, Makromol. Chem., 181, 2305 (1980).
M. Okada, H. Sumitomo, and K. Ogasawara, Polym. J., 14, 815 (1982).
M. Okada, H. Sumitomo, and Y. Hishida, Makromol. Chem., 184, 1823 (1983).
M. Okada, H. Sumitomo, and K. Ogasawara, Polym. J., 15, 821 (1983).
M. Okada, H. Sumitomo, A. Sumi, and T. Sugimoto, Macromolecules, 17, 2451 (1984).
M. Okada, H. Sumitomo, and A. Sumi, Carbohydr. Res., 143, 275 (1985).
F. Shafizadeh, R. H. Furneaux, T. G. Cocharn, J. P. School, Y. Sakai, J. Appl. Polym. Sci., 23, 3525 (1979).
T. Uryu, K. Tachikawa, K. Ohaku, K. Terui, and K. Matsuzaki, Makromol. Chem., 178, 1929 (1977).
F. Sweet and R. K. Brown, Can. J. Chem., 46, 2289 (1968).
M. Okada, H. Sumitomo, and T. Hirasawa, Macromolecules, 18, 2345 (1985).
L. W. Menapace and H. G. Kuivila, J. Am. Chem. Soc., 86, 3047 (1964).
M. Somogy, J. Biol. Chem., 195, 19 (1952).
M. Okada, H. Sumitomo, and A. Sumi, Polym. Bull., 7, 431 (1982).
M. Okada, H. Sumitomo, and A. Sumi, Macromolecules, 15, 1238 (1982).
W. H. Starnes, Jr., F. C. Schilling, K. B. Abbas, I. M. Plitz, R. L. Hartless, and F. A. Borey, Macromolecules, 12, 13 (1979).
W. H. Starnes, Jr., F. C. Schilling, K. B. Abbas, R. E. Cais, and F. A. Bovey, Macromolecules, 12, 556 (1979).
W. H. Starness, Jr., F. C. Schilling, I. M. Plitz, R. E. Cais, and F. A. Bovey, Polym. Bull., 4, 552 (1981).
F. A. Jameison, F. C. Schilling, and A. E. Tonelli, Macromolecules, 19, 2168 (1986).
W. B. Neely, Adv. Carbohyd. Chem., 15, 341 (1960).
R. L. Sidebotham, Adv. Carbohyd. Chem. Biochem., 30, 371 (1974).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Okada, M., Sumitomo, H. & Hirasawa, T. Chemical Synthesis of Polysaccharides. VIII. Synthesis and Enzymatic Hydrolysis of (1→6)-α-Linked Heteropolysaccharides Consisting of D-Glucose and 2,3,4-Trideoxy-DL-glycero-hexopyranose Units. Polym J 19, 581–591 (1987). https://doi.org/10.1295/polymj.19.581
Issue Date:
DOI: https://doi.org/10.1295/polymj.19.581