Preparation and chromatographic performance of chiral peptide-based stationary phases for enantiomeric separation

被引:2
|
作者
Ma, Zhengyue [1 ]
Shang, Panpan [1 ]
Liu, Delu [1 ]
Nie, Yangyang [1 ]
Liu, Yanli [1 ]
Guo, Xinyuan [1 ]
Wei, Benben [1 ]
Bai, Ligai [1 ]
Qiao, Xiaoqiang [1 ,2 ]
机构
[1] Hebei Univ, Coll Pharmaceut Sci, Key Lab Pharmaceut Qual Control Hebei Prov, Baoding, Peoples R China
[2] Hebei Univ, Coll Pharmaceut Sci, Key Lab Pharmaceut Qual Control Hebei Prov, Baoding 071002, Peoples R China
关键词
chiral recognition; enantiomeric separation; peptide chiral stationary phase; phenylalanine; proline; SILICA; ENANTIOSEPARATION; IMPROVEMENT; RESOLUTION; PENDANTS;
D O I
10.1002/chir.23564
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
This study presents the development of three new chiral stationary phases. They are based on silica modified with peptides containing phenylalanine and proline. Successful analyses and characterizations were conducted using Fourier transform infrared spectra, elemental analysis, and thermogravimetric analysis. After this, the enantioselective performance of the three chiral peptide-based columns was evaluated. The evaluation used 11 racemic compounds under normal-phase high performance liquid chromatography mode. Optimized enantiomeric separation conditions were established. Under these conditions, the enantiomers of flurbiprofen and naproxen were successfully separated on CSP-1 column: the separation factor of these was 1.27 and 1.21, respectively. In addition, the reproducibility of the CSP-1 column was also investigated. The results of the investigation illustrated that the stationary phases have good reproducibility (RSD = 0.73%, n = 5).
引用
收藏
页码:636 / 644
页数:9
相关论文
共 50 条
  • [1] ENANTIOMERIC SEPARATION OF ROTENONE AND ROTENOLONE ON CHIRAL STATIONARY PHASES
    ABIDI, SL
    JOURNAL OF LIQUID CHROMATOGRAPHY, 1987, 10 (06): : 1085 - 1102
  • [2] CHIRAL RECOGNITION MODELS OF ENANTIOMERIC SEPARATION ON CYCLODEXTRIN CHIRAL STATIONARY PHASES
    LEE, SH
    KIM, BH
    LEE, YC
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 1995, 16 (04) : 305 - 309
  • [3] Preparation of methylated β-cyclodextrin bonded stationary phases and chromatographic evaluation for chiral separation
    Ryu, JW
    Kim, DW
    Lee, KP
    ANALYTICAL SCIENCES, 1997, 13 : 217 - 220
  • [4] Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases
    Woods, Ross M.
    Patel, Darshan C.
    Breitbach, Zachary S.
    Kurti, Laszlo
    Armstrong, Daniel W.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [5] Enantiomeric separation of biaryl atropisomers using cyclofructan based chiral stationary phases
    Woods, Ross M.
    Patel, Darshan C.
    Lim, Yeeun
    Breitbach, Zachary S.
    Gao, Hongyin
    Keene, Craig
    Li, Gongqiang
    Kuerti, Laszlo
    Armstrong, Daniel W.
    JOURNAL OF CHROMATOGRAPHY A, 2014, 1357 : 172 - 181
  • [6] Chitosan bis(halophenylcarbamate)-(isobutyrylamide) based chiral stationary phases for enantiomeric separation
    Tang, Sheng
    Bin, Qin
    Feng, Zi-Wei
    Chen, Wei
    Huang, Shao-Hua
    Bai, Zheng-Wu
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (11) : 9657 - 9665
  • [7] A study of tetrapeptide enantiomeric separation on crown ether based chiral stationary phases
    Upmanis, T.
    Kazoka, H.
    Arsenyan, P.
    JOURNAL OF CHROMATOGRAPHY A, 2020, 1622
  • [8] SEPARATION OF SOME ENANTIOMERIC DIPEPTIDES AND TRIPEPTIDES ON CHIRAL STATIONARY PHASES
    PIRKLE, WH
    ALESSI, DM
    HYUN, MH
    POCHAPSKY, TC
    JOURNAL OF CHROMATOGRAPHY, 1987, 398 : 203 - 209
  • [9] Preparative chromatographic separation of enantiomers on chiral stationary phases
    Kuesters, E.
    Chimica Oggi, (7-8):
  • [10] Development of chiral stationary phases for high-performance liquid chromatographic separation
    Tang, Mengling
    Zhang, Jing
    Zhuang, Shulin
    Liu, Weiping
    TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 2012, 39 : 180 - 194