Acta Phys. -Chim. Sin. ›› 2009, Vol. 25 ›› Issue (07): 1273-1278.doi: 10.3866/PKU.WHXB20090713

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Host-Guest Interactions of β-Cyclodextrin with Enantiomers of Ethyl α-Chloropropionates

SHI Jie-Hua, XIAO Ke-Ke, LV Yuan-Yuan   

  1. College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, P. R. China|State Key Laboratory Breeding Base of Green Chemistry Synthesis Technology, Zhejiang University of Technology, Hangzhou 310032, P. R. China
  • Received:2009-02-10 Revised:2009-03-12 Published:2009-06-26
  • Contact: SHI Jie-Hua


Host-guest interactions of β-cyclodextrin (β-CD) with enantiomers of ethyl α-chloropropionates ((R/S)-ECPA) were simulated using the quantum mechanics PM3 method. The chiral recognition mechanism of (R/S)-ECPA enantiomers on β-CD was investigated. Modeling results showed that the stabilization of complexes formed by (R/S)-ECPA enantiomers and β-CD were different. (R)-ECPA was located on the cavity wide mouth end of β-CD to form an associated molecule, but (S)-ECPAinserted into the β-CDcavity to forman inclusion molecule. The stabilization energy of the (S)-ECPA and β-CD complex was lower than that of the (R)-ECPA and β-CD complex. The chiral carbon in the ECPA of (R/S)-ECPA and β-CD complexes was close to the C2 and C3 in the glucose unit. The chiral recognition mechanism was thus closely related to the chiral environment provided by C2 and C3 in the glucose unit and the degree of (R/S)-ECPA and β-CD inclusion.

Key words: PM3, Ethyl α-chloropropionate, β-Cyclodextrin, Molecular simulation, Chiral recognization


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