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Chiral separation of phenyllactic acid by helical structure from spring dextrin

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Abstract

We performed the enzymatic synthesis of spring dextrin (SD) with a helical conformation and investigated its chiral-recognition properties in relation to the stereoselective phenyllactic acid (PLA), using reversed-phase high-performance liquid chromatography. The effects of column temperature, buffer pH and methanol content on enantioselective separation were investigated. Baseline chromatographic separation was achieved on an Inertsil ODS-SP column using 1 % SD as the chiral mobile-phase additive. Helical structure was necessary for chiral separation of PLA, according to visible spectroscopy. Molecular dynamic simulations to predict the interactions between SD and PLA showed that van der Waals attractions played an important role in enantiomer separation.

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Acknowledgments

This work was supported by National Natural Science Foundation of China (No. 31401647), Nature Science Foundation of Jiangsu Province (No. BK20140150), Fundamental Research Funds for the Central Universities (JUSRP11449), Program for Changjiang Scholars and Innovative Research Team in University (IRT1135) and Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD, No. 137).

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Authors and Affiliations

  1. Key Laboratory of Eco-textiles of Ministry of Education, College of Textiles and Clothing, Jiangnan University, 1800 Lihu AVE, Wuxi, 214122, People’s Republic of China

    Jin Xu, Qiang Wang & Xuerong Fan

  2. State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, 214122, People’s Republic of China

    Xueming Xu

  3. School of Food Science and Technology, Jiangnan University, 1800 Lihu AVE, Wuxi, 214122, People’s Republic of China

    Xueming Xu

Authors
  1. Jin Xu
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  2. Xueming Xu
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  3. Qiang Wang
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  4. Xuerong Fan
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Correspondence to Xuerong Fan.

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Xu, J., Xu, X., Wang, Q. et al. Chiral separation of phenyllactic acid by helical structure from spring dextrin. J Incl Phenom Macrocycl Chem 82, 515–521 (2015). https://doi.org/10.1007/s10847-015-0487-x

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  • DOI: https://doi.org/10.1007/s10847-015-0487-x

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