Abstract
Two peracylated β-cyclodextrin derivatives, 2,3,6-tri-O-valeryl-β-cyclodextrin and 2,3,6-tri-O-octanoyl-β-cyclodextrin, were synthesized and used as capillary gas chromatography (CGC) chiral stationary phases. The two peracylated β-cyclodextrin derivatives showed enantioseparation abilities to some chiral compounds tested, such as enantiomers of methyl 2-chloropropionate, 5-hydroxy-4, 4-dimethyl-dihydrofuran-2-one, and methyl 2-hydroxypropionate. As CGC chiral stationary phases, the two peracylated β-cyclodextrin derivatives showed excellent enantioseparation abilities to methyl 2-hydroxypropionate (i.e., methyl lactate). On 2,3,6-tri-O-valeryl-β-cyclodextrin, the enantiomer separation factor and resolution of methyl lactate were 1.21 and 6.08, respectively, and on 2,3,6-tri-O-octanoyl-β-cyclodextrin, 1.22 and 5.49, respectively. The enantioseparation results of methyl lactate on the two peracylated β-cyclodextrin derivatives were better than on most reported β-cyclodextrin derivatives, including a commercial chiral column of permethylated β-cyclodextrin tested in this study. Results suggest that CGC methods using 2,3,6-tri-O-valeryl-β-cyclodextrin or 2,3,6-tri-O-octanoyl-β-cyclodextrin as chiral stationary phase could be used for enantioseparation and evaluating the enantiomeric optical purity of methyl lactate.
References
Clary JJ, Feron VJ, Van JA (1998) Regul Toxicol Pharm 27:88–97
Qiu J, Wang QX, Wang P, Jia GF, Li JL, Zhou ZQ (2005) Pest Biochem Physiol 83:1–8
Kikuchi T, Okada M, Nengaki N, Furutsuka K, Wakizaka H, Okamura T, Zhang MR, Kato K (2011) Bioorg Med Chem 19:3265–3273
Li WY, Jin HL, Armstrong DW (1990) J Chromatogr A 509:303–324
Venema A, Tolsma PJA (1989) J High Resol Chromatogr 12:32–34
Shi XY, Liang P, Song DL, Gao XW (2010) Chromatographia 71:539–544
Koenig WA, Icheln D, Hardt I (1991) J High Resol Chromatogr 14:694–695
Zhang Y, Armstrong DW (2011) Analyst 136:2931–2940
Keim W, Kohnes A, Meltzow W, Romer H (1991) J High Resol Chromatogr 14:507–529
Sultana T, Jung JM, Hong SS, Lee WK, Gal YS, Kim HG, Lim KT (2012) J Incl Phenom Macrocycl Chem 72:207–212
Shi XY, Guo HC, Wang M, Jiang SR (2002) Chromatographia 56:207–211
Shi XY, Guo HC, Wang M, Jiang SR (2002) Chromatographia 55:755–759
Zhang HB, Zhang J, Fu RN, Zuo XB, Liu HF (1998) Chromatographia 48:305–309
Koenig WA (1993) J High Resol Chromatogr 16:569–586
Armstrong DW, Li WY, Pitha J (1990) Anal Chem 62:214–217
Acknowledgments
This research was supported by the Application Techniques of Pesticides Efficiently and Safely (200903033-02) (Agricultural Ministry of China), the prevention and control technology research for major fruit and vegetable pests and diseases and integration demonstration (2012BAD19B06) (National Key Technology R&D Program of China), and the Program for China New Century Excellent Talents in University (NCET-06-0113).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shi, X., Liang, P., Song, D. et al. Enantioseparation of Methyl 2-Hydroxypropionate with Two Peracylated β-Cyclodextrin Derivatives as CGC Chiral Stationary Phases. Chromatographia 77, 517–522 (2014). https://doi.org/10.1007/s10337-014-2634-8
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10337-014-2634-8