Abstract
The partition coefficients K av of methylglycopyranosides, deoxysugars and glucooligosaccharides for partition between polystyrene gel and aqueous solvent systems were determined. Each group of sugars showed widely different polystyrene affinities and these affinities increased markedly in NaCl solution but were eliminated in 50% methanol. The K av for methylα-D-mannoside (10.6) was remarkably greater than those of methyl-α-D-glucoside (3.0) and methyl-α-D-galactoside (2.2). Another notable feature was that the polystyrene affinity was affected by the position of the OH-H substitutions in deoxysugars and by the type of the glucosidic linkages of glucodisaccharides. The inspection of the overall K av spectrum together with the accessible surface data of sugar molecules suggests that the hydrophobicity of sugars is determined by a set of several factors including CH-surface area, hydration effect of OH groups and molecular planarity and rigidity.
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References
M. Janado and Y. Yano,J. Solution Chem. 14, 891 (1985).
M. Janado and T. Nishida,J. Solution Chem. 10, 489 (1981).
M. Janado and Y. Yano,Bull. Chem. Soc. Jpn. 58, 1913 (1985).
A. Suggett, inWater, A Comprehensive Treatise, Vol. 4, F. Franks, ed. (Plenum Press, New York, 1975), p. 519.
A. C. Haglund and N. V. B. Marsden,J. Polym. Sci. Polym. Lett. Ed. 18, 217 (1980).
M. Janado, Y. Yano, H. Nakamori, and T. Nishida,J. Chromatogr. 193, 345 (1980).
Y. Yano and M. Janado,J. Chromatogr. 200, 125 (1980).
R. P. Bywater and N. V. B. Marsden,Chromatography Library Series, 22A (Elsevier, Amsterdam, 1983, Chap. 8, p. 257.
M. Janado, inAqueous Size-Exclusion Chromatography, P. L. Dubin, ed. (Elsevier, Amsterdam, in press), Chap. 2.
K. Miyajima, K. Machida, and M. Nakagaki,Bull. Chem. Soc. Jpn. 58, 2595 (1985).
R. B. Hermann,J. Phys. Chem. 76, 2754 (1972).
E. Edmond, S. Farquhar, J. R. Dunstone, and A. G. Ogston,Biochem. J. 108, 775 (1968).
T. C. Laurent and J. Killander,J. Chromatogr. 14, 317 (1964).
M. Dubois, K. A. Gilles, J. K. Hamilton, P. A. Reber, and F. Smith,Anal. Chem. 28, 350 (1956).
B. Lee and F. M. Richards,J. Mol. Biol. 55, 379 (1971).
S. J. Angyal, inAdvances in Carbohydrate Chemistry and Biochemistry, Vol. 42, R. S. Tipson and D. Horton, eds. (Academic Press, New York, 1984), p. 15.
J. E. Desnoyers, M. Arel, G. Perron, and C. Jolicoeur,J. Phys. Chem. 73, 3364 (1969).
C. Tanford, inThe Hydrophobic Effect (John Wiley and Sons, New York, 1973), p. 12.
R. W. Gurney, inIonic Process in Solution (McGraw-Hill, New York, 1954), Chap. 9.
T. T. Herskovits and T. M. Kelly,J. Phys. Chem. 77, 381 (1973).
W. B. Landliker and V. A. de Saussure, inThe Chemistry of Biosurfaces, Vol. 1, M. L. Hair, ed. (Dekker, New York, 1971), p. 1.
M. Janado, Y. Yano, H. Nishida and T. Nishida,J. Solution Chem. 15, 839 (1986).
W. Kauzmann,Advan. in Protein Chem. 14, 1 (1959).
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Yano, Y., Tanaka, K., Doi, Y. et al. The polystyrene affinity of methylglycosides, deoxysugars and glucooligosaccharides. J Solution Chem 17, 347–358 (1988). https://doi.org/10.1007/BF00650415
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DOI: https://doi.org/10.1007/BF00650415