Chiral separations of transition metal complexes using capillary zone electrophoresis

Harris, Jamie E; Desai, Nehal; Seaver, Kathryn E; Watson, Rhett T.; Kane-Maguire, Noel A. P.; Wheeler, John F.

doi:10.1016/s0021-9673(01)00820-2

Cited by 32 publications

(36 citation statements)

References 22 publications

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“…While one study describes the investigation of the enantiomerization of ferroin by preparative enantiomer separation followed by a measurement of the racemization kinetics by polarimetry [155,156], other studies do not describe enantiomerizations for the higher homologs 1,10-phenanthrolin complexes of B VIII group elements [157,158].…”

Section: Metal Complexesmentioning

confidence: 99%

Investigation of the stereodynamics of molecules and catalyzed reactions by CE

Trapp

2010

Electrophoresis

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The investigation of the molecular dynamics of stereoisomers and the study of the kinetics of reactions, in particular of catalyzed reactions, is of fundamental interest in chemistry, biochemistry, and medicine. Understanding how to control the transition state of a reaction allows for a directed design of new catalysts and benign processes. The integration of reactions and capillary or microchip-based electrophoretic separations is highly attractive to perform on-column derivatizations or enzymatic on-column digests of peptides and proteins for further characterization. The present review article focuses on the recent advances to study the stereodynamics of molecules and reaction kinetics of catalyzed processes by means of CE. Models and algorithms to evaluate interconversion profiles obtained by electrophoretic separation techniques are discussed with respect to the challenging demands of high separation efficiencies typical for electrophoretic techniques. Models used for evaluation are based on iterative computer simulation algorithms using the theoretical plate model or stochastic model of chromatography, empirical calculation methods, derived from equations used in chemical engineering, namely Damköhler analysis, and direct access with the approximation function and more recently with the unified equation, which can be applied to all kinds of first-order reactions taking place during a chromatographic or a electrophoretic separation. Furthermore, areas of applications are presented and discussed to give a guideline for using dynamic CE and on-column reaction electrophoresis to study kinetics of reactions and dynamic processes.

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Section: Metal Complexesmentioning

confidence: 99%

Investigation of the stereodynamics of molecules and catalyzed reactions by CE

Trapp

2010

Electrophoresis

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“…30,[54][55][56][57][58][59][60][61][62] There have been relatively few reports on the enantiomeric separation of transition metal poly(diimine) complexes. 30,[56][57][58][59][60][62][63][64] Chiral additives used for the CE separation of transition metal complexes are usually chiral anions, including carboxymethyl-b-cyclodextrin, 30,[56][57][58][59] tartrate and its derivatives, 30,56,57,59 isocitrate and amino acids derivatives 58 and bile salts. 57,58 In our study, nine cyclodextrin based chiral additives were evaluated by CE and micellar CE for the separation of nine tris(diimine)ruthenium(II) complexes and all stereoisomers of a dinuclear ruthenium(II) tris(diimine) complex (see Fig.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of chiral ruthenium(II) complexes using capillary electrophoresis

et al. 2008

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Capillary zone electrophoresis (CZE) and micellar capillary electrophoresis (MCE) were applied for the enantiomeric separation of nine mononuclear tris(diimine)ruthenium(II) complexes as well as the separation of all stereoisomers of a dinuclear tris(diimine)ruthenium(II) complex. Nine cyclodextrin (CD) based chiral selectors were examined as run buffer additives to evaluate their effectiveness in the enantiomeric separation of tris(diimine)ruthenium(II) complexes. Seven showed enantioselectivity. Sulfated gamma-cyclodextrin (SGC), with four baseline and three partial separations, was found to be the most useful chiral selector. In CZE mode, the derivatized gamma-CDs were more effective than beta-CDs while sulfated CDs work better than carboxymethyl CDs. In MCE mode, hydroxypropyl beta-CD separated the greatest number of tris(diimine) ruthenium(II) complexes. The effects of chiral selector concentration, run buffer pH and concentration, the concentration ratio between chiral selector and other factors were investigated.

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“…Enantiomerically-pure deuterated amino acid standards L-2,3, To characterize the compounds using methods described in our previous report, 28 ESI-mass spectra of the selectors were obtained. Both negative ionization mode ESI-mass spectra of synthesized bis(sodium) D 4,8,10, and 8 for the amino acids Ala, Val, Leu, and Phe, respectively). All solutions with chiral selectands and selectors were freshly prepared before ESI-MS analysis.…”

Section: Experimental Section Materialsmentioning

confidence: 99%

ESI‐MS investigation of solvent effects on the chiral recognition capacity of tartar emetic towards neutral side‐chain amino acids

Wijeratne¹,

Yang²,

Gracia³

et al. 2010

Chirality

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The effect of solvent systems on previously-reported ESI-MS based proton-assisted enantioselective molecular recognition phenomena of tartar emetic, L-antimony(III)-tartrate, was evaluated. This was achieved by carrying out a series of competitive binding experiments using chiral selectors, bis(sodium) D- and -L-antimony(III)-tartrates with chiral selectands, neutral side-chain amino acid enantiomeric isotopomers of alanine (Ala), valine (Val), leucine (Leu) and phenylalanine (Phe), in three different solvent systems, ACN/H(2)O (75/25 v/v), H(2)O (100%) and H(2)O/MeOH (25/75 v/v). Observations from these experiments suggest that the effect of solvent systems on previously reported proton-assisted chiral recognition capacity of D,L-antimony(III)-tartrates is small, but not negligible. It was observed that an ACN/H(2)O (75/25 v/v) solvent system facilitates and enhances the chiral discrimination capacity of protonated {[D,L-Sb(2)-tar(2)][H]}(-) ionic species. Further, amino acid enantiomers showed a general trend of increasing selectivity order, Val ≤ Ala < Leu ≈ Phe towards the protonated {[D,L-Sb(2)-tar(2)][H]}(-) ionic species which was independent of the solvent system employed. The lack of enantioselective binding for {[D,L-Sb(2)-tar(2)]}(2-) ionic species was consistently recorded in respective mass spectra from all performed experiments, which suggests that ESI-friendly solvent systems have no effect and do not influence this phenomenon.

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Chiral separations of transition metal complexes using capillary zone electrophoresis

Cited by 32 publications

References 22 publications

Investigation of the stereodynamics of molecules and catalyzed reactions by CE

Investigation of the stereodynamics of molecules and catalyzed reactions by CE

Enantiomeric separation of chiral ruthenium(II) complexes using capillary electrophoresis

ESI‐MS investigation of solvent effects on the chiral recognition capacity of tartar emetic towards neutral side‐chain amino acids

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