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Separation and analysis of cis-diol-containing compounds by boronate affinity-assisted micellar electrokinetic chromatography

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Abstract

Cis-diol-containing compounds (CDCCs) are usually highly hydrophilic compounds and are therefore difficult to separate by conventional reversed-phase-based micellar electrokinetic chromatography (MEKC) due to poor selectivity. Here, we report a new method, called boronate affinity-assisted micellar electrokinetic chromatography (BAA-MEKC), to solve this issue. A boronic acid with a hydrophobic alkyl chain was added to the background electrolyte, which acted as a modifier to adjust the selectivity. CDCCs can covalently react with the boronic acid to form negatively charged surfactant-like complexes, which can partition into micelles formed with a cationic surfactant. Thus, CDCCs can be separated according to the differential partition constants of their boronic acid complexes between the micellar phase and the surrounding aqueous phase. To verify this method, eight nucleosides were employed as the test compounds and their separation confirmed that the combination of boronate affinity interaction with MEKC can effectively enhance the separation of CDCCs. The effects of experimental conditions on the separation were investigated. Finally, the BAA-MEKC method was applied to the separation and analysis of nucleosides extracted from human urine. BAA-MEKC exhibited better selectivity and improved separation as compared with conventional MEKC and CZE. Successful quantitative analysis of urinary nucleosides by BAA-MEKC was demonstrated.

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Acknowledgments

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (Grants No. 21075063 and 21121091), the Natural Science Foundation of Jiangsu Province (Grant No. KB2011054) and the Ministry of Science and Technology of China (Grant No. 35-15).

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Authors and Affiliations

  1. State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China

    Heye Wang, Chenchen Lü, Hengye Li, Yang Chen & Zhen Liu

  2. Department of Hematology, The Affiliated Drum Tower Hospital of Nanjing University Medical School, Nanjing, 210008, China

    Min Zhou & Jian Ouyang

Authors
  1. Heye Wang
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  2. Chenchen Lü
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  3. Hengye Li
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  4. Yang Chen
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  5. Min Zhou
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  6. Jian Ouyang
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  7. Zhen Liu
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Corresponding author

Correspondence to Zhen Liu.

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Wang, H., Lü, C., Li, H. et al. Separation and analysis of cis-diol-containing compounds by boronate affinity-assisted micellar electrokinetic chromatography. Anal Bioanal Chem 405, 8579–8586 (2013). https://doi.org/10.1007/s00216-013-7256-8

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  • DOI: https://doi.org/10.1007/s00216-013-7256-8

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