Enantioseparation by MEKC using a ligand exchange-based chiral pseudostationary phase.
In this paper, a new ligand-exchange -MEKC mode, based on the design of a unique lipohilic species (4'-octadecylneamine derivative), which served both as micelle-forming surfactant (by its hydrophobic part) and central ion-complexing ligand (by its hydrophilic part) is described. The CMC of the used lipophilic neamine derivative was first determined by surface tension measurements. Subsequent NMR experiments were performed in order to investigate the Cu(II) binding properties of the neamine micellar phase. The enantioseparation properties of both the octadecylneamine derivative-Cu(II) MEKC and the native neamine-Cu(II) CE systems were evaluated and compared using the tryptophan racemate as a probe analyte. The effects of several different electrophoretic conditions on the enantiomer migration behavior in the ligand-exchange-MEKC mode were examined. The developed methodology was also applied to the enantioseparation of other analytes such as 1-methyl-tryptophan, 3,5-diiodo-tyrosine and 1-naphtyl-alanine.
Zaher
Mustapha
M
Département de Pharmacochimie Moléculaire UMR 5063 CNRS, Institut de Chimie Moléculaire de Grenoble FR 2607, Université Grenoble I (Joseph Fourier), UFR de Pharmacie, Grenoblex, France.
Ravelet
Corinne
C
Vanhaverbeke
Cecile
C
Baussanne
Isabelle
I
Perrier
Sandrine
S
Fize
Jennifer
J
Décout
Jean-Luc
JL
Peyrin
Eric
E
D002614:Chelating Agents; D020374:Chromatography, Micellar Electrokinetic Capillary / Q000379:methods*; D003300:Copper; D008024:Ligands; D000432:Methanol / Q000737:chemistry; D008823:Micelles; D009355:Neomycin / Q000031:analogs & derivatives; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013500:Surface Tension; D013501:Surface-Active Agents / Q000737:chemistry; D014364:Tryptophan / Q000031:analogs & derivatives / Q000737:chemistry
C545828:4'-octadecylneamine; D002614:Chelating Agents; D008024:Ligands; D008823:Micelles; D013501:Surface-Active Agents; D003300:Copper; D014364:Tryptophan; D009355:Neomycin; D000432:Methanol