Enantiomeric Discrimination of D/L-10-Camphoric Sulfonic Acid by  β-Cyclodextrins Studied by NMR Spectroscopy

Abstract

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.

Key words: NMR, chiral recognition, β-cyclodextrin, camphoric sulfonic acid

CLC Number:

O482.53

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.

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Enantiomeric Discrimination of D/L-10-Camphoric Sulfonic Acid by β-Cyclodextrins Studied by NMR Spectroscopy

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