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

Xue-Xian Chen ,
Li-Ming Yuan ^,

1.
School of Energy and Environment, Yunnan Normal University, Kunming 650500, China

Corresponding author: Li-Ming Yuan,
Received Date: 19 December 2014
Available Online: 27 March 2015
Fund Project: This work was supported by the National Natural Science Foundation of China (No. 21165022). (No. 21165022)

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.
- Mandelic acid,
- Enantioselective,
- Indicator displacement assays,
- Colorimetric enantiodiscrimination
1. [1]
  [1] N.M. Maier, P. Franco, W. Lindner, Separation of enantiomers: needs, challenges, perspectives, J. Chromatogr. A 906 (2001) 3-33.
2. [2]
  [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]
  [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]
  [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]
  [5] A. Kurganov, Chiral chromatographic separations based on ligand exchange, J. Chromatogr. A 906 (2001) 51-71.
6. [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.
7. [7]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [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]
  [14] Y. Okamoto, E. Yashima, Polysaccharide derivatives for chromatographic separation of enantiomers, Angew. Chem. Int. Ed. 37 (1998) 1020-1043.
15. [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.
16. [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.
1. [1]
  Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp³)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
2. [2]
  Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
3. [3]
  Yang Chen , Peng Chen , Yuyang Song , Yuxue Jin , Song Wu . Application of Chemical Transformation Driven Impurity Separation in Experiments Teaching: A Novel Method for Purification of α-Fluorinated Mandelic Acid. University Chemistry, 2024, 39(6): 253-263. doi: 10.3866/PKU.DXHX202310077
4. [4]
  Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
5. [5]
  Junying LI , Xinyan CHEN , Xihui DIAO , Muhammad Yaseen , Chao CHEN , Hao WANG , Chuansong QI , Wei LI . Chiral fluorescent sensor Tb³⁺@Cd-CP based on camphoric acid for the enantioselective recognition of R- and S-propylene glycol. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2497-2504. doi: 10.11862/CJIC.20240084
6. [6]
  Yuxin Wang , Zhengxuan Song , Yutao Liu , Yang Chen , Jinping Li , Libo Li , Jia Yao . Methyl functionalization of trimesic acid in copper-based metal-organic framework for ammonia colorimetric sensing at high relative humidity. Chinese Chemical Letters, 2024, 35(6): 108779-. doi: 10.1016/j.cclet.2023.108779
7. [7]
  Xingfen Huang , Jiefeng Zhu , Chuan He . Catalytic enantioselective N-silylation of sulfoximine. Chinese Chemical Letters, 2024, 35(4): 108783-. doi: 10.1016/j.cclet.2023.108783
8. [8]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
9. [9]
  Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
10. [10]
  Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
11. [11]
  Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp³)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
12. [12]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
13. [13]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
14. [14]
  Guorong Li , Yijing Wu , Chao Zhong , Yixin Yang , Zian Lin . Predesigned covalent organic framework with sulfur coordination: Anchoring Au nanoparticles for sensitive colorimetric detection of Hg(Ⅱ). Chinese Chemical Letters, 2024, 35(5): 108904-. doi: 10.1016/j.cclet.2023.108904
15. [15]
  Jia Chen , Yun Liu , Zerong Long , Yan Li , Hongdeng Qiu . Colorimetric detection of α-glucosidase activity using Ni-CeO₂ nanorods and its application to potential natural inhibitor screening. Chinese Chemical Letters, 2024, 35(9): 109463-. doi: 10.1016/j.cclet.2023.109463
16. [16]
  Caixia Zhu , Qing Hong , Kaiyuan Wang , Yanfei Shen , Songqin Liu , Yuanjian Zhang . Single nanozyme-based colorimetric biosensor for dopamine with enhanced selectivity via reactivity of oxidation intermediates. Chinese Chemical Letters, 2024, 35(10): 109560-. doi: 10.1016/j.cclet.2024.109560
17. [17]
  Yang Qin , Jiangtian Li , Xuehao Zhang , Kaixuan Wan , Heao Zhang , Feiyang Huang , Limei Wang , Hongxun Wang , Longjie Li , Xianjin Xiao . Toeless and reversible DNA strand displacement based on Hoogsteen-bond triplex. Chinese Chemical Letters, 2024, 35(5): 108826-. doi: 10.1016/j.cclet.2023.108826
18. [18]
  Zhichao Zhou , Fuqian Chen , Xiaotong Xia , Dong Ye , Rong Zhou , Lei Li , Tao Deng , Zhenhua Ding , Fang Liu . Developing a fluorescence substrate for HRP-based diagnostic assays with superiorities over the commercial ADHP. Chinese Chemical Letters, 2024, 35(6): 108970-. doi: 10.1016/j.cclet.2023.108970
19. [19]
  Zhiqing Ge , Zuxiong Pan , Shuo Yan , Baoying Zhang , Xiangyu Shen , Mozhen Wang , Xuewu Ge . Novel high-temperature thermochromic polydiacetylene material and its application as thermal indicator. Chinese Chemical Letters, 2024, 35(11): 109850-. doi: 10.1016/j.cclet.2024.109850
20. [20]
  Gengchen Guo , Tianyu Zhao , Ruichang Sun , Mingzhe Song , Hongyu Liu , Sen Wang , Jingwen Li , Jingbin Zeng . Au-Fe₃O₄ dumbbell-like nanoparticles based lateral flow immunoassay for colorimetric and photothermal dual-mode detection of SARS-CoV-2 spike protein. Chinese Chemical Letters, 2024, 35(6): 109198-. doi: 10.1016/j.cclet.2023.109198

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(720)
HTML views(19)

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