Colorimetric enantiodiscrimination of mandelic acid by indicator displacement assay

Xue-Xian Chen Li-Ming Yuan

Citation:  Xue-Xian Chen, Li-Ming Yuan. Colorimetric enantiodiscrimination of mandelic acid by indicator displacement assay[J]. Chinese Chemical Letters, 2015, 26(8): 1019-1021. doi: 10.1016/j.cclet.2015.04.027 shu

Colorimetric enantiodiscrimination of mandelic acid by indicator displacement assay

    通讯作者: Li-Ming Yuan,
  • 基金项目:

    This work was supported by the National Natural Science Foundation of China (No. 21165022). (No. 21165022)

摘要: The colorimetric enantiodiscrimination between mandelic acid and L-proline-Cu (II) is exploited to develop enantioselective indicator displacement assays. The sensitivity of the assay could be tuned by using a colorimetric indicator. The chromophoric ligand, pyrocatechol violet, effectively competes with the mandelic acid guest for open coordination sites on L-proline-Cu (II). The ΔA could be increased to 0.12 by changing the ratio of (+)-and (-)-mandelic acid concentrations that were found to be optimal from the displacement experiments. The resultant enantiomer excess versus ΔA relationship is linear. From the calibration curves, the absorbance values of the unknowns may be calculated for the enantiomeric excess value and the colorimetric enantiodiscrimination of mandelic acid can thus be obtained.

English

  • 
    1. [1] N.M. Maier, P. Franco, W. Lindner, Separation of enantiomers: needs, challenges, perspectives, J. Chromatogr. A 906 (2001) 3-33.[1] N.M. Maier, P. Franco, W. Lindner, Separation of enantiomers: needs, challenges, perspectives, J. Chromatogr. A 906 (2001) 3-33.

    2. [2] T. Ikai, Y. Okamoto, Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography, Chem. Rev. 109 (2009) 6077-6101.[2] T. Ikai, Y. Okamoto, Structure control of polysaccharide derivatives for efficient separation of enantiomers by chromatography, Chem. Rev. 109 (2009) 6077-6101.

    3. [3] M. Sohail, Y.F. Wang, S.X. Wu, et al., Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism, Chin. Chem. Lett. 24 (2013) 695-698.[3] M. Sohail, Y.F. Wang, S.X. Wu, et al., Non-superimposable mirror image crystals of enantiomers by spontaneous resolution and the chiral discrimination mechanism, Chin. Chem. Lett. 24 (2013) 695-698.

    4. [4] M. Huang, W.J. Chen, Y. Zhou, et al., Enantiomeric separations of four basic drugs containing N-alkyl groups by a RP-HPLC system using SBE-β-CD as chiral mobile phase additive, Chin. Chem. Lett. 24 (2013) 840-844.[4] M. Huang, W.J. Chen, Y. Zhou, et al., Enantiomeric separations of four basic drugs containing N-alkyl groups by a RP-HPLC system using SBE-β-CD as chiral mobile phase additive, Chin. Chem. Lett. 24 (2013) 840-844.

    5. [5] A. Kurganov, Chiral chromatographic separations based on ligand exchange, J. Chromatogr. A 906 (2001) 51-71.[5] A. Kurganov, Chiral chromatographic separations based on ligand exchange, J. Chromatogr. A 906 (2001) 51-71.

    6. [6] J. Su, Y.Q. Sun, F.J. Huo, Y.T. Yang, C.X. Yin, Naked-eye determination of oxalate anion in aqueous solution with copper ion and pyrocatechol violet, Analyst 135 (2010) 2918-2923.[6] J. Su, Y.Q. Sun, F.J. Huo, Y.T. Yang, C.X. Yin, Naked-eye determination of oxalate anion in aqueous solution with copper ion and pyrocatechol violet, Analyst 135 (2010) 2918-2923.

    7. [7] X. Zhang, J. Yin, J. Yoon, Recent advances in development of chiral fluorescent and colorimetric sensors, Chem. Rev. 114 (2014) 4918-4959.[7] X. Zhang, J. Yin, J. Yoon, Recent advances in development of chiral fluorescent and colorimetric sensors, Chem. Rev. 114 (2014) 4918-4959.

    8. [8] D. Leung, S.O. Kang, E.V. Anslyn, Rapid determination of enantiomeric excess: a focus on optical approaches, Chem. Soc. Rev. 41 (2012) 448-479.[8] D. Leung, S.O. Kang, E.V. Anslyn, Rapid determination of enantiomeric excess: a focus on optical approaches, Chem. Soc. Rev. 41 (2012) 448-479.

    9. [9] X.X. Liu, Y.S. Zheng, Chiral nitrogen-containing calix[4]crown—an excellent receptor for chiral recognition of mandelic acid, Tetrahedron Lett. 47 (2006) 6357-6360.[9] X.X. Liu, Y.S. Zheng, Chiral nitrogen-containing calix[4]crown—an excellent receptor for chiral recognition of mandelic acid, Tetrahedron Lett. 47 (2006) 6357-6360.

    10. [10] F. Miao, J. Zhou, D. Tian, H. Li, Enantioselective recognition of mandelic acid with (R)-1, 1-bi-2-naphthol-linked calix[4]arene via fluorescence and dynamic light scattering, Org. Lett. 14 (2012) 3572-3575.[10] F. Miao, J. Zhou, D. Tian, H. Li, Enantioselective recognition of mandelic acid with (R)-1, 1-bi-2-naphthol-linked calix[4]arene via fluorescence and dynamic light scattering, Org. Lett. 14 (2012) 3572-3575.

    11. [11] K. Tanaka, T. Tsuchitani, N. Fukuda, A. Masumoto, R. Arakawa, Highly enantioselective fluorescent recognition of mandelic acid derivatives by chiral salen macrocycles, Tetrahedron Asymm. 23 (2012) 205-208.[11] K. Tanaka, T. Tsuchitani, N. Fukuda, A. Masumoto, R. Arakawa, Highly enantioselective fluorescent recognition of mandelic acid derivatives by chiral salen macrocycles, Tetrahedron Asymm. 23 (2012) 205-208.

    12. [12] L. Xu, Y.Y. Yang, Y.Q. Wang, J.Z. Gao, Chiral salen Mn(III) complex-based enantioselective potentiometric sensor for L-mandelic acid, Anal. Chim. Acta 653 (2009) 217-221.[12] L. Xu, Y.Y. Yang, Y.Q. Wang, J.Z. Gao, Chiral salen Mn(III) complex-based enantioselective potentiometric sensor for L-mandelic acid, Anal. Chim. Acta 653 (2009) 217-221.

    13. [13] D.A. Tsioupi, R.I.S. Staden, C.P.K. Christodoulou, Chiral selectors in CE: recent developments and applications, Electrophoresis 34 (2013) 178-204.[13] D.A. Tsioupi, R.I.S. Staden, C.P.K. Christodoulou, Chiral selectors in CE: recent developments and applications, Electrophoresis 34 (2013) 178-204.

    14. [14] Y. Okamoto, E. Yashima, Polysaccharide derivatives for chromatographic separation of enantiomers, Angew. Chem. Int. Ed. 37 (1998) 1020-1043.[14] Y. Okamoto, E. Yashima, Polysaccharide derivatives for chromatographic separation of enantiomers, Angew. Chem. Int. Ed. 37 (1998) 1020-1043.

    15. [15] J.F. Folmer-Andersen, V.M. Lynch, E.V. Anslyn, Colorimetric enantiodiscrimination of α-amino acids in protic media, J. Am. Chem. Soc. 127 (2005) 7986-7987.[15] J.F. Folmer-Andersen, V.M. Lynch, E.V. Anslyn, Colorimetric enantiodiscrimination of α-amino acids in protic media, J. Am. Chem. Soc. 127 (2005) 7986-7987.

    16. [16] X.F. Mei, C. Wolf, Determination of enantiomeric excess and concentration of unprotected amino acids, amines, amino alcohols, and carboxylic acids by competitive binding assays with a chiral Scandium complex, J. Am. Chem. Soc. 128 (2006) 13326-13327.[16] X.F. Mei, C. Wolf, Determination of enantiomeric excess and concentration of unprotected amino acids, amines, amino alcohols, and carboxylic acids by competitive binding assays with a chiral Scandium complex, J. Am. Chem. Soc. 128 (2006) 13326-13327.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1588
  • HTML全文浏览量:  43
文章相关
  • 发布日期:  2015-04-18
  • 收稿日期:  2014-12-19
  • 网络出版日期:  2015-03-27
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章