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β-环糊精手性识别D/L-樟脑磺酸的NMR研究

         

摘要

Chiral recognition of β-cyclodextrin (β-CD) to chiral drug D/L-10-camphoric sulfonic acid (CSA) was investigated using high resolution liquid-state NMR spectroscopy. It was found that CSA can enter the hydrophobic cavity of β-CD and interact with it chirally. The results of 2D ROESY experiments suggested that the enantiomers of CSA enter into the hydrophobic cavity of β-CD from its wide brim, not from its narrow brim. Stoichiometry result showed a 1∶1 complex between the host and the guest. It was demonstrated that β-CD can be used to discriminate the enantiomers of CSA.%利用高分辨液体NMR技术考察了D_2O中β-环糊精与手性药物D/L-樟脑磺酸对映体之间的相互作用, 结果表明樟脑磺酸对映体能够进入β-环糊精的疏水空腔并与之发生手性相互作用. β-环糊精能够手性识别樟脑磺酸对映体. 化学计量关系实验和2D ROESY实验结果表明, 樟脑磺酸对映体的疏水结构只能从β-环糊精疏水空腔的宽口端进入, 并形成化学计量比为1∶1的非对映体络合物.

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