Influence of selector configurations of biselector chiral stationary phases on enantioseparation

被引:3
作者
Zhang Juan [1 ]
Wei Wenjuan [1 ]
Chen Wei [1 ]
Wu Yuanxin [1 ]
Bai Zhengwu [1 ]
机构
[1] Wuhan Inst Technol, Key Lab Green Chem Proc, Minist Educ, Sch Chem Engn & Pharm, Wuhan 430073, Hubei, Peoples R China
关键词
high performance liquid chromatography (HPCL); chiral stationary phase; biselector; configuration; enantioseparation;
D O I
10.3724/SP.J.1123.2010.00971
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In order to investigate the influence of selector configurations of a biselector chiral stationary phase (CSP) on its chiral recognition, a new biselector CSP was prepared in this work using (lS,2S)-(-) -1,2-diphenylethylenediamine (DPEDA) and L-(-)-dibenzoyl tartaric acid (DBTA) as the chiral origins. The enantioseparation ability of the biselector CSP was evaluated towards chiral analytes of different structures under normal, polar organic and reverse phase modes. The chromatographic separation results showed that the enantioseparation ability of the CSP was equivalent to that of another biselector CSP in previous work, which was derived from (1R,2R)-(+) -1,2-DPEDA and L-(-)-DBTA. However, the chiral compounds separated on the two CSPs were not identical. The influence of selector configurations of biselector CSPs on the chiral recognition was discussed. In the event that the two selectors in a biselector CSP were prepared from different chiral compounds, the stereo-configurations of the two selectors cannot simultaneously match the ones of a chiral analyte, thus causing the decrease in the enantioseparation ability of the biselector CSP.
引用
收藏
页码:971 / 976
页数:6
相关论文
共 15 条
  • [1] Chiral recognition mechanisms
    Berthod, A
    [J]. ANALYTICAL CHEMISTRY, 2006, 78 (07) : 2093 - 2099
  • [2] Iuliano A, 2001, EUR J ORG CHEM, V2001, P3523, DOI 10.1002/1099-0690(200109)2001:18<3523::AID-EJOC3523>3.0.CO
  • [3] 2-#
  • [4] Biselector enantioselective stationary phases for HPLC: dependence of the chiral discrimination properties on stereochemistry and chemical nature of each unit of the chiral auxiliary
    Iuliano, A
    Attolino, E
    Salvadori, P
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (16) : 1805 - 1815
  • [5] OPTIMIZATION OF NAPHTHYLETHYLUREA MULTIPLE-BONDED CHIRAL STATIONARY PHASES FOR OPTICAL RESOLUTION OF ENANTIOMERIC AMINO-ACID DERIVATIVES
    IWAKI, K
    YAMAZAKI, M
    NIMURA, N
    KINOSHITA, T
    [J]. JOURNAL OF CHROMATOGRAPHY, 1992, 625 (02): : 353 - 356
  • [6] R-N-(PENTAFLUOROBENZOYL)PHENYLGLYCINE AS A CHIRAL STATIONARY PHASE FOR THE SEPARATION OF ENANTIOMERS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY
    KIP, J
    VANHAPEREN, P
    KRAAK, JC
    [J]. JOURNAL OF CHROMATOGRAPHY, 1986, 356 (03): : 423 - 427
  • [7] Synthesis and evaluation, of a based chiral stationary phase potentiality of the approach and perspectives
    Lecci, C
    Iuliano, A
    [J]. BIOMEDICAL CHROMATOGRAPHY, 2005, 19 (06) : 439 - 446
  • [8] Strategic use of preparative chiral chromatography for the synthesis of a preclinical pharmaceutical candidate
    Leonard, William R., Jr.
    Henderson, Derek W.
    Miller, Ross A.
    Spencer, Glenn A.
    Sudah, Osama S.
    Biba, Mirlinda
    Welch, Christopher J.
    [J]. CHIRALITY, 2007, 19 (09) : 693 - 700
  • [9] Enantiomeric separation and determination of absolute stereochemistry of asymmetric molecules in drug discovery - Building chiral technology toolboxes
    Mcconnell, Oliver
    Bach, Alvin, II
    Balibar, Carl
    Byrne, Neal
    Cai, Yanxuan
    Carter, Guy
    Chlenov, Michael
    Di, Li
    Fan, Kristi
    Goljer, Igor
    He, Yanan
    Herold, Don
    Kagan, Michael
    Kerns, Edward
    Koehn, Frank
    Kraml, Christina
    Marathias, Vasilios
    Marquez, Brian
    McDonald, Leonard
    Nogle, Lisa
    Petucci, Christopher
    Schlingmann, Gerhard
    Tawa, Gregory
    Tischler, Mark
    Williamson, R. Thomas
    Sutherland, Alan
    Watts, William
    Young, Mairead
    Zhang, Mei-Yi
    Zhang, Yingru
    Zhou, Dahui
    Ho, Douglas
    [J]. CHIRALITY, 2007, 19 (09) : 658 - 682
  • [10] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS ON (1R,3R)-TRANS-CHRYSANTHEMIC ACID AND ITS AMIDE DERIVATIVES BONDED TO SILICA-GEL
    OI, N
    NAGASEM
    INDA, Y
    DOI, T
    [J]. JOURNAL OF CHROMATOGRAPHY, 1983, 259 (03): : 487 - 493