SEPARATION AND PURIFICATION TECHNOLOGY
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2020
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IF 5.774
Qi Zhang,Siru Ren,Song Xue,Ang Li,Siyao Liu,Xiaodong Sun
In the field of separation science, the use of tartaric acid-based ionic liquids (TTILs) for chiral separation has not yet been reported. In this work, six novel mono- and di-tetraalkylammonium l -tartrate ILs (TAA- l -TTs) with different alkane chain length were evaluated for their potential as sole chiral selectors in capillary electrophoresis (CE). In comparison with conventional l -tartaric acid ( l -TT) chiral selector, these IL-type chiral selectors exhibit remarkably improved enantioseparation performance, which is even better than most previously reported TT ester-type chiral selectors. Major factors influencing CE separation were investigated, including the background electrolyte (BGE) composition, ILs concentration, type and proportion of organic modifier, buffer pH, etc. The results show that the l -TT-based IL-type chiral selectors prefer a weak acid buffer (150 mM boric acid at pH 4.5) with a high proportion of methanol (80%-90%). The best resolutions (Rs) were obtained when the IL concentration was set at 60 mM. We further carried out a series of comparative experiments and a molecular simulation study to explore the enantiorecognition mechanism of TTILs. The result indicates that the TAA- l -TTs cannot be considered as a simple combination of TAA salt and l -TT. The dissociation degree of TTILs may be an important factor influencing the enantiorecognition process.
研究领域:
分析化学
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分离科学
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产品关联
DOI
高影响因子
JOURNAL OF MASS SPECTROMETRY
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2017
·Vol. 52
·期 7
·411-416
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IF 2.381
L. Wang,Y. Wang,Y. Chai,Y. Kang,C. Sun,S. Zeng
A facile method based on electrospray mass spectrometry was established and validated for the differentiation of enantiomeric tadalafil isomers without using chiral chromatographic separation. The enantiomers were coupled with a chiral selector to form diastereomeric complex ions. Nickel–tadalafil complexes, [Ni II (tadalafil)( l -Trp)-H] + , produced a characteristic fragment ion at m / z 524 by loss of 1-methyl-1,6-dihydropyrazine-2,5-dione via collision-induced dissociation. The relative abundance of this fragment ion to the precursor contributed to differentiate tadalafil enantiomers, and energy-resolved product-ion spectra were applied to determine the molar composition of tadalafil in the mixture ( R , R and S , S ) as well. In addition, the other two forms of stereomeric isomers of tadalafil ( R , S and S , R ) could be also distinguished and analyzed by this method. The method was validated in different types of mass spectrometers (AB quadrupole time-of-flight and Bruker ion trap) and also verified by a chiral high-performance liquid chromatography coupled with quadrupole time-of-flight. The chiral determination of tadalafil using MS method proved to be rapid (1-min run time for each sample) and to have the same accuracy and precision comparable to chiral liquid chromatography mass spectrometry methods. This method provides an alternative to commonly used chromatographic technique for chiral determination and is particularly useful in rapid screening in enantioselective synthesis and enantiomeric impurity detection in pharmaceutical industry. Copyright © 2017 John Wiley & Sons, Ltd.
研究领域:
分析化学
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药物化学
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质谱分析
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产品关联
DOI
PubMed
高影响因子
ANALYTICA CHIMICA ACTA
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2017
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IF 4.95
Xiangying Yu,Zhong-Ping Yao
In this study, travelling wave ion mobility mass spectrometry has been used to investigate chiral differentiation of common chiral amino acids , through separation of binuclear copper bound tetrameric ions formed with chiral selector tryptophan , proline , tyrosine , phenylalanine or histidine . Significant chiral recognition was observed for amino acids with aromatic rings or long and active side chains, with peak-to-peak resolutions up to 1.826. Tryptophan and histidine offered better enantioselectivity , compared to other chiral selectors. The results suggested that the mechanism for chiral recognition in ion mobility mass spectrometry might be significantly different from that in tandem mass spectrometry . Linear calibration curves were also established to allow determination of enantiomeric excess of the analytes by the approach. This study showed that higher assembly of chiral analyte and chiral selector might enable better chiral discrimination and ion mobility mass spectrometry could be a powerful technique for provide qualitative, quantitative and structural information of chiral analysis.
研究领域:
分析化学
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生物化学
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产品关联
DOI
PubMed
高影响因子
NEW JOURNAL OF CHEMISTRY
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2018
·Vol. 42
·期 16
·13520-13528
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IF 3.201
Shujuan Xu,Yuying Wang,Yixia Tang,Yibing Ji
A new mixed selector chiral stationary phase (CSP) was prepared with co-immobilized human serum albumin and cellulase on a poly(glycidylmethacrylate-co-ethylene glycol dimethacrylate) (poly(GMA-co-EDMA)) monolith and the evaluation of its usefulness in chiral separation research was presented. For comparison, two single selector chiral stationary phases (CSPs) were also fabricated with the corresponding proteins. The enantioseparation ability of these CSPs was investigated by capillary electrochromatography (CEC) with various racemates. The mixed selector CSP exhibited a broader range of enantioselectivities than the single selectors and it could separate 10 chiral analytes while the two single selector CSPs resolved 3 and 8 respectively. Moreover, for (±)-warfarin, the enantioresolution was improved on the mixed selector CSP. Meanwhile, compared with the single selector CSPs, no additional preparation stage or reagent consumption was required in the simultaneous immobilization of different proteins, which is more favorable from economical and practical points of view. Consequently, by mixing HSA and cellulase together, the composite column combines the enantioselectivities of both individual proteins, thus expanding their application range practically.
研究领域:
分析化学
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生物化学
✓ 已验证
DOI
高影响因子
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