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Chromatographic Properties of 2,3-Di-O-allyl-6-O-acyl-β-cyclodextrins as Chiral Stationary Phases of Capillary GC

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Abstract

Three 2,3-di-O-allyl-6-O-acyl-β-cyclodextrins, 2,3-di-O-allyl-6-O-valeryl-β-cyclodextrin, 2,3-di-O-allyl-6-O-heptanoyl-β-cyclodextrin, and 2,3-di-O-allyl-6-O-octanoyl-β-cyclodextrin, were synthesized and their chromatographic properties were investigated. 2,3-di-O-allyl-6-O-acyl-β-cyclodextrins cannot only separate the enantiomers of methyl 2-chloropropionate, methyl 2-bromopropionate, methyl 2-hydroxypropionate, allethrone acetate, propargyllone acetate, and 1-(2,4-dichlorophenyl)ethanol, but also possess enantiomer separation abilities to some enantiomers of pyrethroic acid methyl esters and epoxides. The enantiomer separation results on the three 2,3-di-O-allyl-6-O-acyl-β-CDs were used to draw some empirical rules about enantiomer separation together with the enantiomer separation results on other CDs. Acyl groups on CDs, especially 3-position acyl groups on CDs, are favorable for the enantiomer separation of pyrethroic acid methyl esters, while acyl groups on 6-position of CDs are beneficial for the enantiomer separation of epoxides, but allyl on CDs are less favorable for enantiomer separation than pentyl. The empirical rules summarized here have some practice significances in selecting CGC chiral stationary phase for solving enantiomer separation problems. Also, the three 2,3-di-O-allyl-6-O-acyl-β-CDs may be used in practical chiral analysis.

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Acknowledgments

The project described was kindly supported by the Program for New Century Excellent Talents in University of China (NCET-06-0113), the National Natural Science Foundation of China (NSFC-30771426), and the National Basic Research Program of China (2006CB102003).

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Authors and Affiliations

  1. Department of Entomology, China Agricultural University, 2 Yuanmingyuan West Road, 100193, Beijing, China

    Xueyan Shi, Pei Liang, Dunlun Song & Xiwu Gao

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  1. Xueyan Shi
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  2. Pei Liang
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  3. Dunlun Song
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  4. Xiwu Gao
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Correspondence to Xiwu Gao.

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Shi, X., Liang, P., Song, D. et al. Chromatographic Properties of 2,3-Di-O-allyl-6-O-acyl-β-cyclodextrins as Chiral Stationary Phases of Capillary GC. Chroma 71, 539–544 (2010). https://doi.org/10.1365/s10337-010-1473-5

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