Separation of enantiomers by capillary electrophoresis using pentosan polysulfate

Wang, Xiande; Lee, Jauh Tzuoh; Armstrong, Daniel W.

doi:10.1002/(sici)1522-2683(19990101)20:1<162::aid-elps162>3.0.co;2-6

Cited by 37 publications

(4 citation statements)

References 26 publications

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“…Negatively charged polysaccharides such as heparin, chondroitin sulfate C, chondroitin sulfate A, dextran sulfate and l-carrageenan have been used for the chiral separation of bases [375]. More recently investigated selectors on the basis of sulfated glycosaminoglycan are dermatan sulfate DS (chondroitin sulfate B) [381], a fucose containing glycosaminoglycan (FGAG) and a depolymerized holothurian glycosaminoglycan (DHG) [382] and pentosan polysulfate [383].…”

Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Neutral CD Derivatives a Great Variety Of Neutral Derivativmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

View full text Add to dashboard Cite

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“…At higher pH values, enantioselectivity would be expected to diminish as the dianionic form is populated. Other reports in the literature also assert the importance of pH on enantioselective solution phase separations [27][28][29]. With regard to mass spectrometry, these findings may prompt further evaluation of previous work using antimony(III)-tartrates in ESI-based enantioselective association experiments [14,15] [30], but to our knowledge, this is the first report of such behavior for small molecule enantioselective binding systems, recorded in both solution-phase targeting ESI-MS and gas-phase MS/MS dissociation experiments.…”

Section: Th Values (mentioning

confidence: 99%

Antimony(III)-D, L-tartrates exhibit proton-assisted enantioselective binding in solution and in the gas phase

Wijeratne

Miko

Gracia

et al. 2009

J. Am. Soc. Mass Spectrom.

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The negative ion mode ESI mass spectral analysis of antimony(III)-D-and -L-tartrate ("tartar emetic"), in association with leucine enantiomeric isotopomers, revealed remarkable protonassisted enantioselective molecular recognition phenomena. The current study infers that recognition of amino acids by antimony(III)-D,L-tartrate complexes requires that the chiral selector associate a proton to become enantioselective. The dianionic selector itself failed to show enantiomeric discrimination capacity. This observation was shown to be consistent both in solution-phase targeting full scan and gas-phase targeting collision threshold dissociation (CTD) experiments. Importantly, this disparity in enantioselective binding capacity between the dianionic and the protonated monoanionic representatives of antimony(III)-D-and -L-tartrates could only be clearly revealed by ESI-MS and tandem mass spectrometry experiments as described herein. This finding urges a more in-depth study of mechanisms associated with exhibited enantiomeric resolving capacity of antimony tartrates in HPLC and CE applications, as well as in former ESI-MS association studies. (J Am Soc Mass Spectrom 2009, 20, 2100 -2105

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“…Its average molecular mass range is 5000 . For its high degree of esterification with sulfuric acid, pentosan polysulfate (PPS) exhibits more ionizable groups per monomer unit than heparin . PPS consists of repeating linear units of (1–4)‐linked β‐D xylanopyranoses in which α‐D‐4‐methylglucopyranosyluronic acid units are glycosidically linked to the second position of every tenth xylanopyranose unit on average (Fig.…”

Section: Introductionmentioning

confidence: 99%

Using affinity capillary electrophoresis and computational models for binding studies of heparinoids with p‐selectin and other proteins

et al. 2017

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A fast and precise affinity capillary electrophoresis (ACE) method has been developed and applied for the investigation of the binding interactions between P-selectin and heparinoids as potential P-selectin inhibitors in the presence and absence of calcium ions. Furthermore, model proteins and vitronectin were used to appraise the binding behavior of P-selectin. The normalized mobility ratios (∆R/R ), which provided information about the binding strength and the overall charge of the protein-ligand complex, were used to evaluate the binding affinities. It was found that P-selectin interacts more strongly with heparinoids in the presence of calcium ions. P-selectin was affected by heparinoids at the concentration of 3 mg/L. In addition, the results of the ACE experiments showed that among other investigated proteins, albumins and vitronectin exhibited strong interactions with heparinoids. Especially with P-selectin and vitronectin, the interaction may additionally induce conformational changes. Subsequently, computational models were applied to interpret the ACE experiments. Docking experiments explained that the binding of heparinoids on P-selectin is promoted by calcium ions. These docking models proved to be particularly well suited to investigate the interaction of charged compounds, and are therefore complementary to ACE experiments.

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Separation of enantiomers by capillary electrophoresis using pentosan polysulfate

Cited by 37 publications

References 26 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Antimony(III)-D, L-tartrates exhibit proton-assisted enantioselective binding in solution and in the gas phase

Using affinity capillary electrophoresis and computational models for binding studies of heparinoids with p‐selectin and other proteins

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