Indirect chiral separation of tryptophan enantiomers by high performance liquid chromatography with indirect chemiluminiscence detection

Zhou, Jie; Chen, Shanshan; Sun, Fei; Luo, Pei; Du, Qizhen; Zhao, S. J.

doi:10.1016/j.jchromb.2015.10.017

Cited by 18 publications

(11 citation statements)

References 10 publications

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“…Figure 6C represents the differential CD spectra of l -Trp and d -Trp interacting with N-CDs/β-CD nanocomposites. The strong absorption peaks of Trp enantiomers near 220 nm are attributed to the n − π * transition that occurs mainly due to NH–C=O stretching vibration and benzene ring of Trp enantiomers [6]. On the other hand, N-CDs/β-CD nanocomposites exhibit almost no absorption in the same wavelength range.…”

Section: Resultsmentioning

confidence: 99%

“…Since the natural amino acids in human beings are predominantly l -isomers and the presence of d -isomers in life forms usually indicates negative symptoms, the discrimination of amino acid enantiomers is thus of great interest and increasing importance in chemical, biological and pharmaceutical sciences [5,6]. Several analytical techniques have been explored for the enantiomers’ separation, such as high-performance liquid chromatography [6], capillary electrophoresis [7,8], and fluorescence spectrometry [9]. However, these methods require expensive chiral columns, relatively long analysis times and complicated sample pre-treatments.…”

Section: Introductionmentioning

confidence: 99%

“…l -Tryptophan ( l -Trp), which plays a predominant role in all life forms, is a vital constituent of most proteins and precursor of serotonin, niacin and auxins [6,9]. On the other side, as a non-protein amino acid, d -Tryptophan ( d -Trp) often presents different activity, toxicity and metabolic routes [12].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Novel N-Doped Carbon Dots/β-Cyclodextrin Nanocomposites for Enantioselective Recognition of Tryptophan Enantiomers

Xiao¹,

Lu²,

Huang³

et al. 2016

Sensors

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Based on N-doped carbon dots/β-cyclodextrin nanocomposites modified glassy carbon electrodes (N-CDs/β-CD/GCE), an effective electrochemical sensor for enantioselective recognition of tryptophan (Trp) enantiomers was developed by differential pulse voltammograms (DPVs). Fluorescent N-CDs were synthesized through a hydrothermal method and characterized by spectroscopic approaches. The N-CDs/β-CD nanocomposites were efficiently electrodeposited on the surface of GCE through C–N bond formation between N-CDs and electrode. The obtained N-CDs/β-CD/GCE was characterized by multispectroscopic and electrochemical methods. Such N-CDs/β-CD/GCE generated a significantly lower Ip and more negative Ep in the presence of l-Trp in DPVs, which was used for the enantioselective recognition of Trp enantiomers. The N-CDs/β-CD nanocomposites showed different binding constants for tryptophan enantiomers, and they further selectively bonded with l-Trp to form inclusion complexes. This N-CDs/β-CD/GCE combined advantages of N-CDs with strong C–N binding ability and β-CD with specific recognition of Trp enantiomers to fabricate a novel sensing platform for enantioselective recognition of Trp enantiomers. This strategy provided the possibility of using a nanostructured sensor to discriminate the chiral molecules in bio-electroanalytical applications.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Novel N-Doped Carbon Dots/β-Cyclodextrin Nanocomposites for Enantioselective Recognition of Tryptophan Enantiomers

Xiao¹,

Lu²,

Huang³

et al. 2016

Sensors

View full text Add to dashboard Cite

show abstract

“…This interest is due to the different pharmacokinetic characteristics and pharmacological activities of each enantiomer in a racemic drug. Many different types of instrumentation and methods have been utilized for enantioseparation, including HPLC , GC , and CE . Compared to HPLC and GC, CE offers advantages of high separation efficiency, rapid analytical time, and low sample volume.…”

Section: Introductionmentioning

confidence: 99%

A novel in situ strategy for the preparation of a β‐cyclodextrin/polydopamine‐coated capillary column for capillary electrochromatography enantioseparations

Guo

Niu

Pan

et al. 2017

J of Separation Science

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Inspired by the chiral recognition ability of β-cyclodextrin and the natural adhesive properties of polydopamine under alkaline conditions, in this study, a rapid and in situ modification strategy was developed to fabricate β-cyclodextrin/polydopamine composite material coated-capillary columns for open tubular capillary electrochromatography. The results of scanning electron microscopy, FTIR spectroscopy, streaming potential, and electro-osmotic flow studies indicated that β-cyclodextrin/polydopamine was successfully fixed on the inner wall of the capillary column. This coating can be achieved within 1 h affording a greatly reduced capillary preparation time. The performance of the β-cyclodextrin/polydopamine-coated capillary was validated by the analysis of seven pairs of chiral analytes, namely epinephrine, norepinephrine, isoprenaline, terbutaline, verapamil, tryptophane, carvedilol. Good enantioseparation efficiencies were achieved for all. For three consecutive runs, the relative standard deviations for the migration times of the analytes for intraday, interday, and column-to-column repeatability were in the range of 0.41-1.74, 1.03-4.18, and 1.66-8.24%, respectively. Moreover, the separation efficiency of the β-cyclodextrin/polydopamine-coated capillary column did not decrease obviously over 90 runs. The strategy should also be feasible to introduce and immobilize other chiral selectors on the inner walls surface of capillary columns.

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“…Chiral separation is a subject of prime importance in pharmaceutical and related industries. [1] The methods to isolate the desired enantiomer from its racemic mixture are available for selection, including crystallization methods, [2,3] chromatographic techniques, [4,5] membrane-based approaches [6][7][8][9] and so on. [10] These available techniques have significantly contributed to the development of the field.…”

Section: Introductionmentioning

confidence: 99%

Study on kinetics of reactive extraction of propranolol enantiomers by multiple linear regression method

Zhang

Cheng

Tang

et al. 2017

Asia-Pacific J Chem Eng

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Kinetic study on reactive extraction of propranolol (Pra) enantiomers with di-cyclohexyl (D)-tartrate (DT) and boric acid (BA) as combined chiral selector was performed in a modified Lewis cell. The effects of agitation speed, interfacial area, pH value of aqueous phase, as well as initial concentrations of DT, BA and Pra enantiomers on extraction rate were investigated. The experimental data were analyzed by multiple linear regression method to evaluate some important parameters. It was found that the interfacial reaction is 0.4, 0.8 and 0.8 order separately with respect to BA, Pra and DT, and the forward rate constants have been found to be 5.08 × 10 À4 L/(mol s) for (R)-Pra and 2.42 × 10 À4 L/(mol s) for (S)-Pra. An interfacial reaction mechanism was proposed to understand the rate equation.

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Indirect chiral separation of tryptophan enantiomers by high performance liquid chromatography with indirect chemiluminiscence detection

Cited by 18 publications

References 10 publications

Novel N-Doped Carbon Dots/β-Cyclodextrin Nanocomposites for Enantioselective Recognition of Tryptophan Enantiomers

Novel N-Doped Carbon Dots/β-Cyclodextrin Nanocomposites for Enantioselective Recognition of Tryptophan Enantiomers

A novel in situ strategy for the preparation of a β‐cyclodextrin/polydopamine‐coated capillary column for capillary electrochromatography enantioseparations

Study on kinetics of reactive extraction of propranolol enantiomers by multiple linear regression method

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