Comparative study of three teicoplanin-based chiral stationary phases using the linear free energy relationship model

被引:22
作者
Lokajová, J
Tesarová, E
Armstrong, DW
机构
[1] Charles Univ, Fac Sci, Dept Phys & Macromol Chem, Prague 12843, Czech Republic
[2] Iowa State Univ, Dept Chem, Ames, IA USA
关键词
LFER; HPLC; chiral stationary phases; macrocyclic glycopeptide; teicoplanin; teicoplanin aglycon; methylated teicoplanin aglycon;
D O I
10.1016/j.chroma.2005.03.105
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Teicoplanin (T) is a macrocyclic glycopeptide that is highly effective as a chiral selector for enantiomeric separations. In this study, we used three teicoplanin-based chiral stationary phases (CSPs)-native teicoplanin, teicoplanin aglycon (TAG) and recently synthesized methylated teicoplanin aglycon (MTAG). In order to examine the importance of various interaction types in the chiral recognition mechanism the three related CSPs were evaluated and compared using a linear free energy relationship (LFER). The capacity factors of 19 widely different solutes, with known solvation parameters, were determined on each of the columns under the same mobile phase conditions used for the chiral separations. The regression coefficients obtained revealed the magnitude of the contribution of individual interaction types to the retention on the compared columns under those specific experimental conditions. Statistically derived standardized regression coefficients were used to evaluate the contribution of individual molecular interactions within one stationary phase. It has been concluded that intermolecular interactions of the hydrophobic type significantly contribute to retention on all the CSPs studied here. Other retention increasing factors are n- and pi-electron interactions and dipole-dipole or dipole-induced dipole ones, while hydrogen donating or accepting interactions are more predominant with the mobile phase than with the stationary phases. However, these types of interactions are not equally significant for all the CSPs studied. (c) 2005 Elsevier B.V. All rights reserved.
引用
收藏
页码:57 / 66
页数:10
相关论文
共 30 条
[2]   THE USE OF CHARACTERISTIC VOLUMES TO MEASURE CAVITY TERMS IN REVERSED PHASE LIQUID-CHROMATOGRAPHY [J].
ABRAHAM, MH ;
MCGOWAN, JC .
CHROMATOGRAPHIA, 1987, 23 (04) :243-246
[3]   HYDROGEN-BONDING .16. A NEW SOLUTE SOLVATION PARAMETER, PI-2(H), FROM GAS-CHROMATOGRAPHIC DATA [J].
ABRAHAM, MH ;
WHITING, GS ;
DOHERTY, RM ;
SHUELY, WJ .
JOURNAL OF CHROMATOGRAPHY, 1991, 587 (02) :213-228
[4]   Characterization of some GLC chiral stationary phases: LFER analysis [J].
Abraham, MH .
ANALYTICAL CHEMISTRY, 1997, 69 (04) :613-617
[5]   Characterizing ionic liquids on the basis of multiple solvation interactions [J].
Anderson, JL ;
Ding, J ;
Welton, T ;
Armstrong, DW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14247-14254
[6]  
[Anonymous], J CHEM SOC P2
[7]  
[Anonymous], UNPUB
[8]   Concentration dependence of lumped mass transfer coefficients - Linear versus non-linear chromatography and isocratic versus gradient operation [J].
Antos, D ;
Kaczmarski, K ;
Piatkowski, W ;
Seidel-Morgenstern, A .
JOURNAL OF CHROMATOGRAPHY A, 2003, 1006 (1-2) :61-76
[9]   MACROCYCLIC ANTIBIOTICS AS A NEW CLASS OF CHIRAL SELECTORS FOR LIQUID-CHROMATOGRAPHY [J].
ARMSTRONG, DW ;
TANG, YB ;
CHEN, SS ;
ZHOU, YW ;
BAGWILL, C ;
CHEN, JR .
ANALYTICAL CHEMISTRY, 1994, 66 (09) :1473-1484
[10]   QUANTITATIVE STRUCTURE RETENTION RELATIONSHIP APPROACH TO PREDICTION OF LINEAR SOLVATION ENERGY RELATIONSHIP COEFFICIENTS .1. H-BOND ACCEPTOR CAPABILITY OF GAS-CHROMATOGRAPHY STATIONARY PHASES IN MCREYNOLDS DATA SET [J].
BALLANTINE, DS .
JOURNAL OF CHROMATOGRAPHY, 1993, 628 (02) :247-259