Enantioselective Recognition of Chiral Α-Phenylethanol by Β-Cyclodextrin and Characterization of its Inclusion Behaviour based on 2D ROESY

Author:

Chen Jian1,Li Qiulin2,Yang Yawen2,Qi Liang1,Han Xiang2,Zhang Nan2,Zheng Bin2,Chen Fuxin2

Affiliation:

1. School of Food Science and Engineering, Shaanxi University of Science and Technology, Xi’an, 710021, Shaanxi, China

2. School of Chemistry and Chemical Engineering, Xi’an University of Science and Technology, Xi’an, 710054, Shaanxi, China

Abstract

Background: α-phenylethanol and its derivatives are important intermediates for the synthesis of a variety of chiral drugs. Methods: The interaction mechanism of the two enantiomers of α-phenylethanol with β-cyclodextrin (β-CD) was investigated using 1H-NMR and ROESY. The loading of β-CD as the host with the chiral drug intermediate α-phenylethanol as the guest was investigated using high-resolution NMR in D2O and quantum chemical calculations. Results: The results showed that both α-phenylethanol enantiomers were able to enter into the hydrophobic cavity of β-CD and undergo enantiospecific interactions, while the combination of 2D ROESY and quantum chemical calculations showed that the benzene ring of both R and S α- phenylethanol were inserted into the β-CD cavity toward the small-port end. However, the most stable poses of the two enantiomers were different, so the benzene ring of the S-enantiomer was more inclined to position the small-port end of β-CD than that of the R-enantiomer, which was reflected differently in the signals of 2D ROESY. Conclusion: β-CD can enantioselectively recognize the α-phenylethanol enantiomers, and the 2D ROESY method is a direct and powerful tool in the recognition process of chiral host and guest research.

Funder

National Natural Science Foundation of China

Shaanxi Natural Science Foundation

Scientific Research Plan Project of Education Department of Shaanxi

China Postdoctoral Science Foundation

General Plan Project of Department of Science and Technology of Shaanxi Province

Publisher

Bentham Science Publishers Ltd.

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