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β-环糊精手性识别D/L-樟脑磺酸的NMR研究
引用本文:黄少华,柏正武,冯继文.β-环糊精手性识别D/L-樟脑磺酸的NMR研究[J].波谱学杂志,2009,26(4):457-465.
作者姓名:黄少华  柏正武  冯继文
作者单位:1.波谱与原子分子物理国家重点实验室,武汉磁共振中心(中国科学院 武汉物理与数学研究所),湖北 武汉 430071;2.中国科学院 研究生院,北京 100049;3.武汉工程大学 化工与制药学院,湖北 武汉 430073
基金项目:国家自然科学基金资助项目(10474116,10674152)
摘    要:利用高分辨液体NMR技术考察了D2O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.

关 键 词:核磁共振(NMR)    手性识别    β-环糊精    樟脑磺酸  
收稿时间:2009-05-30
修稿时间:2009-06-10

Enantiomeric Discrimination of D/L-10-Camphoric Sulfonic Acid by  β-Cyclodextrins Studied by NMR Spectroscopy
HUANG Shao-Hua,BAI Zheng-Wu,FENG Ji-Wen.Enantiomeric Discrimination of D/L-10-Camphoric Sulfonic Acid by  β-Cyclodextrins Studied by NMR Spectroscopy[J].Chinese Journal of Magnetic Resonance,2009,26(4):457-465.
Authors:HUANG Shao-Hua  BAI Zheng-Wu  FENG Ji-Wen
Institution:1.State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics,  Wuhan Center for Magnetic Resonace,(Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences), Wuhan 430071, China; 2.Graduate School of the Chinese Academy of Sciences, Beijing 100049, China; 3.School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430073, Chin
Abstract: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.
Keywords:NMR  chiral recognition  &beta  -cyclodextrin  camphoric sulfonic acid
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