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Effect of the Type of Glycosidic Linkage on the Selective Interactions of Maltose and Cellobiose with Some Crown Ethers in Dilute Aqueous Solutions

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Abstract

Titration calorimetric and densimetric measurements have been applied to study the selective interactions of two disaccharides composed of two glucose units, maltose and cellobiose, with 15-crown-5 and 18-crown-6 in dilute aqueous solutions. Maltose and cellobiose form thermodynamically stable complexes with different stoichiometries with 18-crown-6 but not with 15-crown-5. The obtained results are explained by the different states of the disaccharides in aqueous solution due to effect of the type of linkage between glucose units

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References

  1. Laine, R.A.: Glycosciences: Status and Perspectives. Gabius, H.-J. and Gabius, S. (eds.) Chapman & Hall, Weinheim-London (1997), pp. 1–14

    Google Scholar 

  2. Robertson, A., Shinkai, S.: Cooperative binding in selective sensors, catalysts and actuators. Coord. Chem. Rev. 205, 157–199 (2000)

    Article  CAS  Google Scholar 

  3. Rhalou, T., Ferhat, M., Frouji, M.A., Langevin, D., Métayer, M., Verchère, J.-F.: Molecular recognition of carbohydrates by a resorcinarene. Selective transport of alditols through a supported liquid membrane. Carbohydr. Res. 329, 409–422 (2000)

    Article  Google Scholar 

  4. Davidova, O.I., Lebedeva, N.Sh., Parfenyuk, E.V.: Calorimetric study of binding of some dusaccharides with crown ethers. Thermochim. Acta 421, 31–33 (2004)

    Article  Google Scholar 

  5. Volkova, N.L., Parfenyuk, E.V.: Selective interactions of 18-crown-6 with D-glucose and D-galactose in aqueous solutions: Titration calorimetry, densimetry, viscosimetry. Thermochim. Acta 435, 108–112 (2005)

    Article  CAS  Google Scholar 

  6. Volkova, N.L., Lebedeva, N.Sh., Parfenyuk, E.V.: Complexation of D-xylose and L-arabinose with 18-crown-6 in aqueous solutions: Calorimetric, densimetric, and viscosimetric studies. Russ. J. Coord. Chem. 31, 899–903 (2005)

    Article  CAS  Google Scholar 

  7. Volkova, N.L. Parfenyuk, E.V.: Parameters of complex formation in triple solutions D-glucose or D-galactose -15-crown-5 – water. Russ. J. Phys. Chem. (2006), in press.

  8. Lebedeva, N.Sh., Mikhailovskii, K.V., V’ugin, A.I.: Differential automatic titration calorimeter. Russ. J. Phys. Chem. 75, 1031–1033 (2001)

    Google Scholar 

  9. Abrosimov V.K.: Non-extrapolated method of determination of partial molar volumes and isentropic compressibilities at infinite dilution. Russ. J. Phys. Chem. 62, 1913–1916 (1988) (in Russian)

    CAS  Google Scholar 

  10. Hiraoka, M.: Crown Compounds. Elsevier Science Publishers Company, Amsterdam (1982)

    Google Scholar 

  11. Fukahara, K., Tachikake, M., Matsumoto, S.: Raman spectroscopic study of the hydrates of 18-crown-6. J. Phys. Chem. 99, 8617–8623 (1995)

    Article  Google Scholar 

  12. Fenrau-Dupont, J., Declercq, J.P., Germain, G., Meersche, M.V.: Complexe 1:1 pentaoxa-1,4,7,10,13-cyclopentadécane-bromure cuire (II) hydrate. Acta Crystallogr. B35, 1215–1217 (1979)

    Article  Google Scholar 

  13. Dorman, D.E., Roberts, J.E.: Nuclear magnetic resonance spectroscopy. Carbon-13 spectra of some common oligosaccharides. J. Am. Chem. Soc. 93, 4463–4472 (1971)

    Article  Google Scholar 

  14. Almond, A.: Towards understanding the interactions between oligosaccharide and water molecules. Carbohydr. Res. 340, 907–920 (2005)

    Article  CAS  Google Scholar 

  15. Stevens, E.S., Sathyanarayana, B.K.: Potential energy surfaces of cellobiose and maltose in aqueous solution: A new treatment of disaccharide optical rotation. J. Am. Chem. Soc. 111, 4149–4154 (1989)

    Article  CAS  Google Scholar 

  16. Brady, J. W., Schmidt, R.K.: The role of hydrogen bonding in carbohydrates: Molecular dynamics simulations of maltose in aqueous solution. J. Phys. Chem. 97, 958–966 (1993)

    Article  CAS  Google Scholar 

  17. Kačurϡkovϡ, M., Mathlouthi, M.: FTIR and laser–Raman spectra of oligosaccharides in water: Characterization of the glycosidic bond. Carbohydr. Res. 284, 145–157 (1996)

    Article  Google Scholar 

  18. Bock, K.: Carbohydrate-protein interactions: Substrate specificity of enzymes used in the degradation of oligosaccharides related to starch and cellulose. Pure and Appl. Chem. 59, 1447–1456 (1987)

    CAS  Google Scholar 

  19. Storts, C.A., Cerezo, A.S.: Depicting the MM3 potential energy surfaces of trisaccharides by single contour maps: Application to β-cellotriose and α-maltotriose. Carbohydr. Res. 338, 95–107 (2003)

    Article  Google Scholar 

  20. Lepri, A., Marchettini, N., Pogliani, L., Rossi, C., Ulgiati, S.: NMR structural investigation of cellobiose and glucose. 25, 521–523 (1987)

    CAS  Google Scholar 

  21. Gurney, R.W.: Ionic Process in Solution. McGraw-Hill, New York (1953)

    Google Scholar 

  22. Galema, S.A., Høiland, H.: Stereochemical aspects of hydration of carbohydrates in aqueous solutions. 3. Density and ultrasound measurements. J. Phys. Chem. 95, 5321–5326 (1991)

    Article  CAS  Google Scholar 

  23. Furuki, T.: Effect of molecular structure on thermodynamic properties of carbohydrates. A calorimetric study of aqueous di- and oligosaccharides at subzero temperatures. Carbohydr. Res. 337, 441–450 (2002)

    Article  CAS  Google Scholar 

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  1. Institute of Solution Chemistry of the Russian Academy of Sciences, 1 Akademicheskaya Str., Ivanovo, 153045, Russian Federation

    Elena V. Parfenyuk & N. Sh. Lebedeva

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  1. Elena V. Parfenyuk
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  2. N. Sh. Lebedeva
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Correspondence to Elena V. Parfenyuk.

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Parfenyuk, E.V., Lebedeva, N.S. Effect of the Type of Glycosidic Linkage on the Selective Interactions of Maltose and Cellobiose with Some Crown Ethers in Dilute Aqueous Solutions. J Solution Chem 36, 97–105 (2007). https://doi.org/10.1007/s10953-006-9096-z

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  • DOI: https://doi.org/10.1007/s10953-006-9096-z

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