Yang Zi-Xin, Chen Yong, Liu Yu
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
Carbohydr Res. 2008 Sep 22;343(14):2439-42. doi: 10.1016/j.carres.2008.06.018. Epub 2008 Jul 2.
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 (1)H 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.
通过核磁共振氢谱（¹H NMR）和元素分析研究了环六糖、环七糖和环八糖（α-、β-和γ-环糊精）对双酚A（BPA，一种内分泌干扰化学物质）的包合络合行为及增溶效果。结果表明，β-环糊精和γ-环糊精对双酚A具有良好的增溶能力，其增溶量分别高达7.2×10³ mg L⁻¹和9.0×10³ mg L⁻¹。还采用X射线晶体学衍射和旋转 Overhauser 效应光谱（ROESY）研究了β-环糊精/双酚A包合络合物在水溶液和固态中的结构。结果表明，该络合物在固态中采用2:2化学计量比，即头对头的β-环糊精二聚体容纳两个双酚A分子。双酚A的包合导致β-环糊精空腔的去溶剂化以及β-环糊精二级侧圆形封闭氢键网络的破坏，这使得络合物更易溶解。
