Journal
CARBOHYDRATE RESEARCH
Volume 343, Issue 14, Pages 2439-2442Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2008.06.018
Keywords
cyclodextrin; bisphenol A; solubilization; single-crystal X-ray structure
Funding
- 973 Program [2006CB932900]
- NNSFC [20421202, 20673061, 20772062]
- Key Project of Chinese Ministry of Education [107026]
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The inclusion complexation behavior and the solubilization effects of Bisphenol A (BPA, an endocrine-disrupting chemical) by cyclomaltohexaose, -heptaose, and -octaose (alpha-, beta-, and gamma-cyclodextrins) were investigated by H-1 NMR spectroscopy and by elemental analysis. The results showed that beta- and gamma-cyclodextrins gave the satisfactory solubilization ability to BPA up to 7.2 x 10(3) mg L-1 and 9.0 x 10(3) mg L-1, respectively. X-ray crystallographic diffraction and ROESY spectroscopy were also employed to investigate the structure of the beta-CD/BPA inclusion complex in both aqueous solution and the solid state. The result showed that this complex adopted a 2:2 stoichiometry in the solid state, that is, a head-to-head beta-CD dimer accommodated two BPA molecules. The inclusion of BPA led to the desolvation of the beta-CD cavity and the destruction of the circularly closed hydrogen-bond network in the secondary side of beta-CD, which made the complex more soluble. (C) 2008 Elsevier Ltd. All rights reserved.
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