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Chiral separation of racemates of drugs and amino acid derivatives by high-performance liquid chromatography on a norvancomycin-bonded chiral stationary phase
Ding, GS; Huang, XJ; Liu, Y; Wang, JD
KeywordColumn Liquid Chromatography Norvancomycin-bonded Stationary Phase Chiral Separation Neutral And Basic Drugs
Source PublicationCHROMATOGRAPHIA
2004-04-01
DOI10.1365/s10337-004-190-3
Volume59Issue:7-8Pages:443-449
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Life Sciences & Biomedicine ; Physical Sciences
WOS SubjectBiochemical Research Methods ; Chemistry, Analytical
WOS Research AreaBiochemistry & Molecular Biology ; Chemistry
WOS KeywordCAPILLARY-ELECTROPHORESIS ; MACROCYCLIC ANTIBIOTICS ; TEICOPLANIN ; ENANTIOMERS ; SELECTORS ; VANCOMYCIN ; RETENTION ; DIMERIZATION ; TEMPERATURE ; MODEL
AbstractA novel norvancomycin-bonded chiral stationary phase (NVC-CSP) has been synthesized by use of the chiral selector norvancomycin, which differs from vancomycin because of the presence of leucine rather N-methylleucine. The enantiomers of some neutral and basic chiral drugs, for example warfarin, benzoin, bend roflumethiazide, and praziquantel, were directly separated by high-performance liquid chromatography in the reversed-phase mode. The effect of conditions such as organic modifier concentration, column temperature, pH, and mobile phase flow rate on retention and enantioselectivity were investigated. It was shown that hydrophobic, steric, and ionic interactions were present between the analyte and the macrocycle in this chromatographic system. Van't Hoff plots afforded the thermodynamic data Delta(R),SDeltaH(o) and DeltaR,SDeltaS(o); the negative values obtained indicated the process of enantiomer separation was enthalpy-controlled. In an attempt to improve the resolution of some very polar acidic compounds (donsyl-amino acids) norvancomycin was used as stationary phase chiral selector and chiral mobile-phase additive simultaneously, better results were obtained as the result of a 'synergistic' effect. It was also shown experimentally that the newly synthesized NVC-CSP behaved somewhat differently from the earlier reported vancomycin-banded CSP, probably because of the different structures of norvancomycin and vancomycin.
Language英语
WOS IDWOS:000224100000008
Citation statistics
Cited Times:17[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/139497
Collection中国科学院大连化学物理研究所
AffiliationChinese Acad Sci, Dalian Inst Chem Phys, Dalian 116012, Peoples R China
Recommended Citation
GB/T 7714
Ding, GS,Huang, XJ,Liu, Y,et al. Chiral separation of racemates of drugs and amino acid derivatives by high-performance liquid chromatography on a norvancomycin-bonded chiral stationary phase[J]. CHROMATOGRAPHIA,2004,59(7-8):443-449.
APA Ding, GS,Huang, XJ,Liu, Y,&Wang, JD.(2004).Chiral separation of racemates of drugs and amino acid derivatives by high-performance liquid chromatography on a norvancomycin-bonded chiral stationary phase.CHROMATOGRAPHIA,59(7-8),443-449.
MLA Ding, GS,et al."Chiral separation of racemates of drugs and amino acid derivatives by high-performance liquid chromatography on a norvancomycin-bonded chiral stationary phase".CHROMATOGRAPHIA 59.7-8(2004):443-449.
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