Separation and Analysis of Mixed Amino Acid Enantiomers by Capillary Electrochromatography-Electrospray- Time of Flight/Mass Spectrometry

doi:10.11944/j.issn.1000-0518.2019.07.190021

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (7): 823-831.DOI: 10.11944/j.issn.1000-0518.2019.07.190021

• Full Papers • Previous Articles Next Articles

Separation and Analysis of Mixed Amino Acid Enantiomers by Capillary Electrochromatography-Electrospray- Time of Flight/Mass Spectrometry

LI Yingjie,LIN Xiaotong,GAO Lidi(),QIN Shili,TANG Yimin,JIN Zhixiang,ZHANG Shuai

College of Chemistry and Chemical Engineering,Qiqihar University,Qiqihar,Heilongjiang 161006,China

Received:2019-01-22 Accepted:2019-04-26 Published:2019-07-01 Online:2019-07-02
Contact: GAO Lidi
Supported by:
Supported by the Heilongjiang Provincial Department of Education Overseas Scholars Research Funding Project(No.1254HQ012), Heilongjiang Provincial Department of Education Basic Business Special Science and Engineering Project(No.135209215)

Abstract

Abstract:

A simple and efficient capillary electrochromatography-electrospray- time of flight/mass spectrometry(CEC-ESI-TOF/MS) method for the separation and analysis of mixed amino acid enantiomers was established. D,L-arginine, D,L-valine, and D,L-glutamate acid were taken as the research objects. By optimizing the CEC separation conditions and MS detection conditions, the six components of the three mixed amino acid enantiomers were separated within 15 min, and the resolutions were 3.03, 1.59 and 1.37, respectively. It provides a reference method for the separation and analysis of mixed enantiomers.

Key words: capillary electrochromatography-electrospray-time of flight/mass spectrometry, enantiomer separation, mixed amino acid, monolithic column

LI Yingjie,LIN Xiaotong,GAO Lidi,QIN Shili,TANG Yimin,JIN Zhixiang,ZHANG Shuai. Separation and Analysis of Mixed Amino Acid Enantiomers by Capillary Electrochromatography-Electrospray- Time of Flight/Mass Spectrometry[J]. Chinese Journal of Applied Chemistry, 2019, 36(7): 823-831.

References

[1]	SUN Yaming,BI Qing,WANG Litao,et al. Research Progress of Capillary Electrophoresis in Chiral Amino Acid Resolution[J]. Anal Test Technol Instrum,2015,21(3):129-139(in Chinese). 孙亚明,毕青,王利涛,等. 毛细管电泳在手性氨基酸拆分中的研究进展[J]. 分析测试技术与仪器,2015,21(3):129-139.
[2]	ZHANG Chunyu,LI Yingjie,HAO Xiuju,et al. Chiral Separation of Enantiomers of Four Amino Acids and Two Chial Drugs Through Capillary Electrophoresis[J]. Chinese J Appl Chem,2011,28(11):1340-1342(in Chinese). 张春雨,李英杰,郝秀菊,等. 毛细管电泳法手性拆分4种氨基酸和2种手性药物对映体[J]. 应用化学,2011,28(11):1340-1342.
[3]	Giuffrida A,Maccarrone G,Cucinotta V,et al. Recent Advances in Chiral Separation of Amino Acids Using Capillary Electromigration Techniques[J]. J Chromatogr A,2014,1363:41-50.
[4]	Schurig V.Gas Chromatographic Enantioseparation of Derivatized α-Amino Acids on Chiral Stationary Phases-Past and Present[J]. J Chromatogr B Analyt Technol Biomed Life Sci,2011,879(29):0-3140.
[5]	Müller C,Fonseca J R,et al. Enantioseparation and Selective Detection of D-Amino Acids by Ultra-High-Performance Liquid Chromatography/Mass Spectrometry in Analysis of Complex Biological Samples[J]. J Chromatogr A,2014,1324:109-114.
[6]	Visser W F,erhoeven-Duif N M,Ophoff R,et al. VA Sensitive and Simple Ultra-High-Performance-Liquid Chromatography-Tandem Mass Spectrometry Based Method for the Quantification of D-Amino Acids in Body Fluids[J]. J Chromatogr A,2011,1218(40):7130-7136.
[7]	Gogami Y,Okada K,Oikawa T.High-Performance Liquid Chromatography Analysis of Naturally Occurring D-Amino Acids in Sake[J]. J Chromatogr B Analyt Technol Biomed Life Sci,2011,879(29):0-3267.
[8]	LI Yingjie,ZHAO Nan,GAO Lidi,et al. Preparation of β-Cyclodextrin Derivative Chiral Stationary Phase and Their Application in Capillary Electrochromatography-Mass Spectrometry[J]. J Anal Sci,2018,34(3):377-381(in Chinese). 李英杰,赵楠,高立娣,等. β-环糊精衍生物手性固定相的制备及其在毛细管电色谱-质谱中的应用[J]. 分析科学学报,2018,34(3):377-381.
[9]	LIU Shuren,LI Yingjie,GAO Lidi,et al. Enatio-Separation of Two Kinds of β2-Adrenergic Receptor by CEC-ESI-TOF/MS[J]. Chem Res Appl,2017,29(7):945-950(in Chinese). 刘树仁,李英杰,高立娣,等. CEC-ESI-TOF/MS手性分离两种β2-受体激动剂的研究[J]. 化学研究与应用,2017,29(7):945-950.
[10]	LI Yingjie,XU Hongmei,GAO Lidi,et al. Separation and Analysis of Chiral Drugs Mixture by Capillary Electrochromatography-Electrospray-Time-of-Flight/Mass spectrometry[J]. J Instrum Anal,2018,34(3):377-381(in Chinese). 李英杰,徐红梅,高立娣,等. 毛细管电色谱-电喷雾-飞行时间/质谱联用分离分析混合手性药物[J]. 分析测试学报,2015,34(06):691-695.
[11]	Wang S Y,Wang Y Y,Zhou J,et al. Mono-6'-(4-Methoxybutylamino)-6'-β-Cyclodextrin as a Chiral Selector for Enantiomeric Separation[J]. J Sep Sci,2014,37(15):2056-2061.
[12]	LI Yingjie,LIANG Hui,LV Renjiang,et al. One-Step Preparation and Properties of Allyl-β-Cyclodextrin Chiral Monolithic Capillary Electrochromatography Column[J]. Sci China Ser B,2010,40(11):1682-1687(in Chinese). 李英杰,梁辉,吕仁江,等. 烯丙基-β-环糊精基手性毛细管电色谱整体柱的一步法制备及其性能[J]. 中国科学:化学,2010,40(11):1682-1687.
[13]	LI Yingjie,TANG Yimin,GAO Lidi,et al. Preparation and Application of a New Monolithic Capillary Column for Enantioseparation by CEC-MS[J]. Chem Res Appl,2019.(in Chinese). 李英杰,唐艺旻,高立娣,等. 一种新型毛细管电色谱整体柱的制备及其在CEC-MS中的应用[J]. 化学研究与应用,2019.
[14]	Al-Hussin A,Boysen R I,Saito K,et al. Preparation and Electrochromatographic Characterization of New Chiral β-Cyclodextrin Poly(Acrylamidopropyl) Porous Layer Open Tubular Capillary Columns[J]. J Chromatogr A,2014,1358:199-207.
[15]	Dittmann M M,Rozing G P.Capillary Electrochromatography:Investigation of the Influence of Mobile Phase and Stationary Phase Properties on Electroosmotic Velocity, Retention, and Selectivity[J]. J Microcolumn Sep,2015,9(5):399-408.

Separation and Analysis of Mixed Amino Acid Enantiomers by Capillary Electrochromatography-Electrospray- Time of Flight/Mass Spectrometry

RichHTML

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 4

Recommended Articles

Metrics

Comments

[1]	LV Renjiang, DING Huimin, LI Yingjie*, DING Shuang, DENG Lei, HOU Xuegong. Preparation and Application of Acryla-mide-β-cyclodextrin chiral Monolithic Column for Capil-lary Electrochromatography [J]. Chinese Journal of Applied Chemistry, 2012, 29(05): 604-607.
[2]	LI Xiqian1, MA Huihui2, TONG Shanshan2, JIA Qiong2*. Application of Polymer Monolithic Column in the Pretreatment of Biological Samples Prior to Separation and Analysis [J]. Chinese Journal of Applied Chemistry, 2011, 28(09): 986-992.
[3]	LI Ying-Jie, HAO Xiu-Ju*, ZHANG Chun-Yu, LIANG Hui. Preparation and Application of the Poly-methyl-propyl-butyl acrylate/SiO2/TiO2 Organic-inorganic Hybrid Capillary Monolithic Column [J]. Chinese Journal of Applied Chemistry, 2010, 27(12): 1457-1461.
[4]	LI Ying-Jie*, SUN Feng, GAO Li-Di. Enantiomeric separation of 1-dimethyl-3-phenylpropylamine by Pressurized Capillary electrochromatography [J]. Chinese Journal of Applied Chemistry, 2010, 27(02): 246-248.