Full-text resources of PSJD and other databases are now available in the new Library of Science.
Visit https://bibliotekanauki.pl


Preferences help
enabled [disable] Abstract
Number of results


2006 | 4 | 2 | 223-233

Article title

Theoretical studies on the binding affinities of β-cyclodextrin to small molecules and monosaccharides


Title variants

Languages of publication



Equilibrium geometries and electronic structures of complexes between β-cyclodextrin (β-CD) and some small molecules as well as monosaccharides were investigated by Austin Model 1 (AM1) to obtain binding energy of the complexes. It was indicated that β-CD could bind the structurally similar solvent molecules and monosaccharides because of the negative binding energy of the complexes, and especially could show the chiral binding ability to monosaccharides with more hydroxyl groups, due to its chiral characteristics. The complexes were stabilized by the hydrogen bonding between β-CD and guests. Based on the AM1 optimized geometries, the IR spectra were calculated by AM1 method. Vibration frequencies of O-H bonds in the guests were red-shifted owing to the weakening of the O-H bonds with the formation of the complexes.










Physical description


1 - 6 - 2006
1 - 6 - 2006


  • Department of Chemistry, Zhejiang University, Hangzhou, 310027, People’s Republic of China
  • Department of Chemistry, Zhejiang University, Hangzhou, 310027, People’s Republic of China
  • Department of Chemistry, Zhejiang University, Hangzhou, 310027, People’s Republic of China


  • [1] J. Saejtli: Cyclodextrin Technology, Kluwer-Academic, Dordrecht, 1988, p. 17.
  • [2] G. Wenz: “Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units”, Angew. Chem. Int. Ed. Engl., Vol. 33, (1994), pp. 803–822. http://dx.doi.org/10.1002/anie.199408031[Crossref]
  • [3] Y. Liu and L. Li: “Molecular recognition of supramolecular system. The recent development in the study on molecular recognition and molecular assembly using cyclodextrin as an acceptor”, Prog. Nat. Sci., Vol. 10, (2000), pp. 961–968.
  • [4] X.X. Fan, Y. Yang, S.M. SHuang and C. Dong: “Molecular recognition of β-cyclodextrin to choral amino acids based on methyl orange as a molecular probe”, Spectrochim. Acta A, Vol. 61, (2005), pp. 953–959.
  • [5] B.Y. Xia, W.S. Cai, X.G. Shao, Q.X. Guo, B. Maigret and Z.X. Pan: “Chiral recognition study for the inclusion complexes of amino acids with α-cyclodextrin using a fast annealing evolutionary algorithm”, J. Mol. Stru.: Theochem., Vol. 546, (2001), pp. 33–38.
  • [6] T. Oshikiri, Y. Takashima, H. Yamaguchi and A. Harada: “Kinetic control of threading of cyclodextrins onto axle molecules”, J. Am. Chem. Soc., Vol. 127, (2005), pp. 12186–12187. http://dx.doi.org/10.1021/ja053532u[Crossref]
  • [7] Y.H. Choi, C.H. Yang, H.W. Kim and S. Jung: “Monte Carlo simulations of the chiral recognition of fenoprofen enantiomers by cyclomaltoheptaose(β-cyclodextrin)”, Carbohyd. Res., Vol. 328, (2000), pp. 393–397.
  • [8] H. Asanuma, T. Akiyama, K. Kajiya, T. Hishiya and M. Komiyama: “Molecular imprinting of cyclodextrin in water for the recognition of nanometer-scaled guests”, Anal. Chim. Acta, Vol. 435, (2001), pp. 25–33. http://dx.doi.org/10.1016/S0003-2670(00)01303-9[Crossref]
  • [9] H.J. Qiu: “Spectral analysis of β-cyclodextrin and cationic yellow X-6G inclusion compound”, Text. Auxiliaries, Vol. 20, (2003), pp. 51–53.
  • [10] K.S. Song, C.R. Hou, L. Liu, X.S. Li and Q.X. Guo: “A quantum-chemical study on the molecular recognition of β-cyclodextrin with ground and excited xanthones”, J. Photochem. Photobiol. A: Chem., Vol. 139, (2001), pp. 105–109. http://dx.doi.org/10.1016/S1010-6030(01)00385-9[Crossref]
  • [11] Y. Liu, B. Li, T. Wada and Y. Inoue: “Studies on molecular recognition in supramolecular systems. Part 31: circular dichroism spectral studies of molecular and chiral recognition of aliphatic alcohols by 6-modified β-cyclodextrin”, Tetrahedron, Vol. 57, (2001), pp. 7153–7161. [Crossref]
  • [12] Y. Song and Y. Liu: “Cooperative binding of dyes by biquinolino modified β-cyclodextrin dimers”, Acta Chim. Sinica, Vol. 63, (2005), pp. 103–108.
  • [13] Y. Chen, L. Li and Y. Liu: “Size and shape recognition of dye molecules by organoselenium-bridged bis(cyclodextrin)s”, Chem. J. Chinese Universities, Vol. 23, (2002), pp. 1091–1093.
  • [14] Z. Fan, Y. Zhao and Y. Liu: “Molecular self-assembly behavior of mono[6-oxy-6-(4-carboxylicbenzene)]-β-cyclodextrin in the solution and solid state”, Chin. Sci. Bull., Vol. 48, (2003), pp. 1495–1498.
  • [15] K.B. Lipkowitz: “Applications of computational chemistry to the study of cyclodextrins”, Chem. Rev., Vol. 98, (1998), pp. 1829–1873. http://dx.doi.org/10.1021/cr9700179[Crossref]
  • [16] A.R. Katritzky, D.C. Fara, H. Yang, M. Karelson, T. Suzuki, V.P. Solov’ev and A. Varnek: “Quantitative structure-property relationship modeling of β-cyclodextrin complexation free energies”, J. Chem. Inf. Comput. Sci., Vol. 44, (2004), pp. 529–541. [Crossref]
  • [17] R. Musioł and T. Girek: “Inclusion-dependent mechanism of modification of cyclodextrins with heterocycles”, Cent. Eur. J. Chem., Vol. 3, (2005), pp. 742–746. [Crossref]
  • [18] Q.W. Teng, S. Wu, S.Q. Chen, Y.D. Zhang and X.M. Zheng: “Molecular recognition and “on-off” switching of cyclobis(paraquat-p-phenylene) to neutral guests”, Chem. J. Chinese Universities, Vol. 23, (2002), pp. 1331–1334.
  • [19] S. Wu, Q.W. Teng, X.F. Chen and R.H. Zhou: “Molecular recognition and on-off switching of calix[4]arenes to monosaccharides pyridine derivatives”, Chem. J. Chinese Universities, Vol. 24, (2003), pp. 1271–1273.
  • [20] L.Y. Qi, Q.W. Teng, S. Wu and Z.Z. Liu: “Study on molecular recognition of crown ethers to aniline and monosaccharides”, Chinese J. Struct. Chem., Vol. 24, (2005), pp. 537–540.
  • [21] L.Y. Qi, Q.W. Teng, S. Wu and Z.Z. Liu: “Molecular recognition and “On-off” switching of 30-crown-10 to biological-polar guest molecules”, Chem. J. Chinese Universities, Vol. 26, (2005), pp. 1909–1912.
  • [22] L.L. Zhu, Q.W. Teng and S. Wu: “Study on UV, IR and NMR Spectra of Double Hydrogen-bonded Complexes”, Chinese J. Struct. Chem., Vol. 25(2), (2006), pp. 143–148.
  • [23] L.L. Zhu, Q.W. Teng and S. Wu: “Studies on Hydrogen-Bonding Complexes of Melamine and Cyclotrione”, Chem. J. Chinese Universities, Vol. 27(3), (2006), to be published.
  • [24] M.J. Frisch et al.: Gaussian 03, Revision B.01, Gaussian Inc., Pittsburgh, PA, 2003.
  • [25] Y.M. Zhang and T.B. Wei: “Study on Inclusion Compounds of β-Cyclodextrin with α-and β-Naphthol”, J. Northwest Normal University (Nature Science), Vol. 36, (2000), pp. 70–74.

Document Type

Publication order reference


YADDA identifier

JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.