Chiral separation of amino acids and glycyl dipeptides by chiral ligand-exchange capillary electrophoresis comparing Cu(II), Co(II), Ni(II) and Zn(II) complexes of three different sugar acids

被引:56
作者
Hoedl, Heike [1 ]
Schmid, Martin G. [1 ]
Guebitz, Gerald [1 ]
机构
[1] Karl Franzens Univ Graz, Dept Pharmaceut Chem, Inst Pharmaceut Sci, A-8010 Graz, Austria
关键词
CE; enantiomer separation; ligand-exchange; metal ions; sugar acids; amino acid enantiomers; glycyl dipeptide enantiomers;
D O I
10.1016/j.chroma.2008.05.071
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
This paper deals with comparative studies on the use of copper(II), cobalt(II), nickel(II) and zinc(II) complexes of D-gluconic acid, D-saccharic acid and L-threonic acid as chiral selectors for the enantioseparation of aromatic amino acids and glycyl dipeptides using the principle of ligand-exchange capillary electrophoresis. Although copper(II) is the most frequently used central ion in ligand-exchange capillary electrophoresis, in the case of D-gluconic acid cobalt(II) was shown to be an alternative for the enantioseparation of amino acids. Glycyl dipeptides, however, were resolved only with copper(II) complexes. Zn(II) as a central ion was not effective in all cases and with Ni(II) only some partial separations were achieved. (c) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:210 / 218
页数:9
相关论文
共 26 条
[1]   Coordination properties of 3-functionalized β-cyclodextrins.: Thermodynamic stereoselectivity of copper(II) complexes of the A, B-diamino derivative and its exploitation in LECE [J].
Cucinotta, V ;
Giuffrida, A ;
Maccarrone, G ;
Messina, M ;
Puglisi, A ;
Rizzarelli, E ;
Vecchio, G .
DALTON TRANSACTIONS, 2005, (16) :2731-2736
[2]   3-amino derivative of β-cyclodextrin:: thermodynamics of copper(II) complexes and exploitation of its enantioselectivity in the separation of amino acid racemates by ligand exchange capillary electrophoresis [J].
Cucinotta, V ;
Giuffrida, A ;
La Mendola, D ;
Maccarrone, G ;
Puglisi, A ;
Rizzarelli, E ;
Vecchio, G .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2004, 800 (1-2) :127-133
[3]   Ligand exchange chiral separations by cyclodextrin derivatives in capillary electrophoresis [J].
Cucinotta, V ;
Giuffrida, A ;
Grasso, G ;
Maccarrone, G ;
Vecchio, G .
ANALYST, 2003, 128 (02) :134-136
[4]   LIGAND CHROMATOGRAPHY AS A NOVEL METHOD FOR INVESTIGATION OF MIXED COMPLEXES - STEREOSELECTIVE EFFECTS IN ALPHA-AMINO ACID COPPER(II) COMPLEXES [J].
DAVANKOV, VA ;
ROGOZHIN, SV .
JOURNAL OF CHROMATOGRAPHY, 1971, 60 (02) :280-&
[5]   ELECTROKINETIC SEPARATION OF CHIRAL COMPOUNDS [J].
GASSMANN, E ;
KUO, JE ;
ZARE, RN .
SCIENCE, 1985, 230 (4727) :813-814
[6]   ELECTROKINETIC RESOLUTION OF AMINO-ACID ENANTIOMERS WITH COPPER(II) ASPARTAME SUPPORT ELECTROLYTE [J].
GOZEL, P ;
GASSMANN, E ;
MICHELSEN, H ;
ZARE, RN .
ANALYTICAL CHEMISTRY, 1987, 59 (01) :44-49
[7]   Recent advances in chiral separation principles in capillary electrophoresis and capillary electrochromatography [J].
Gübitz, G ;
Schmid, MG .
ELECTROPHORESIS, 2004, 25 (23-24) :3981-3996
[8]   Advances in chiral separation using capillary electromigration techniques [J].
Guebitz, Gerald ;
Schmid, Martin G. .
ELECTROPHORESIS, 2007, 28 (1-2) :114-126
[9]   Chiral separation of sympathomimetics and β-blockers by ligand-exchange CE using Cu(II) complexes of L-tartaric acid and L-threonine as chiral selectors [J].
Hoedl, Heike ;
Krainer, Axel ;
Holzmueller, Katja ;
Koidl, Julia ;
Schmid, Martin G. ;
Guebitz, Gerald .
ELECTROPHORESIS, 2007, 28 (15) :2675-2682
[10]   Optical resolution of new quinolone drugs by capillary electrophoresis with ligand-exchange and host-guest interactions [J].
Horimai, T ;
Ohara, M ;
Ichinose, M .
JOURNAL OF CHROMATOGRAPHY A, 1997, 760 (02) :235-244