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Citation: SHI Jie-Hua, XIAO Ke-Ke, LV Yuan-Yuan. Host-Guest Interactions of β-Cyclodextrin with Enantiomers of Ethyl α-Chloropropionates[J]. Acta Physico-Chimica Sinica, ;2009, 25(07): 1273-1278. doi: 10.3866/PKU.WHXB20090713 shu

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

1.
College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, P. R. China

Received Date: 10 February 2009
Available Online: 24 April 2009

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.
- PM3,
- Ethyl α-chloropropionate,
- β-Cyclodextrin,
- Molecular simulation,
- Chiral recognization
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