Chiral Separations Using a Polypeptide and Polymeric Dipeptide Surfactant Polyelectrolyte Multilayer Coating in Open-Tubular Capillary Electrochromatography

Kamande, Mary W.; Zhu, Xiaofeng; Kapnissi‐Christodoulou, Constantina P.; Warner, Isiah M.

doi:10.1021/ac049313t

Cited by 53 publications

(47 citation statements)

References 47 publications

(77 reference statements)

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“…Another approach of forming immobilized stationary phase of OT-CEC, multilayer coating of FS capillary by a polypeptide, poly(L-lysine) hydrobromide, and the polymeric dipetide surfactant, poly(sodium undecanoyl-Lleucyl-alaninate), has been used for chiral separations of b-blockers and some other chiral compounds [177].…”

Section: Electrochromatographymentioning

confidence: 99%

“…These selectors are mostly used in the countercurrent, partial filling mode, where the solutes reach the detection cell window after the chiral selector has been displaced from the window region, minimizing the background absorbance from the chiral selector and improving sensitivity [294] but they can be also used as immobilized chiral stationary phase in CEC [295,296]. Physically adsorbed stationary phase consisting of poly(L-lysine) and polymeric dipeptide surfactant, poly(sodium undecanoyl-L-leucyl-alaninate), has been used for OT-CEC separation of b-blockers, labetalol and sotalol, and some other chiral compounds [177].…”

Section: Chiral Analysis and Stereoisomer Separationsmentioning

confidence: 99%

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Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

2006

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The article gives a comprehensive review on the recent developments in the applications of high-performance capillary electromigration methods, zone electrophoresis, isotachophoresis, isoelectric focusing, affinity electrophoresis, electrokinetic chromatography, and electrochromatography, to analysis, preparation, and physicochemical characterization of peptides. The article presents new approaches to the theoretical description and experimental verification of electromigration behavior of peptides, covers the methodological aspects of capillary electroseparations of peptides, such as rational selection of separation conditions, sample preparation, suppression of peptide adsorption, new developments in individual separation modes, and new designs of detection systems. Several types of applications of capillary electromigration methods to peptide analysis are presented: conventional qualitative and quantitative analysis, purity control, determination in biomatrices, monitoring of chemical and enzymatical reactions and physical changes, amino acid and sequence analysis, and peptide mapping of proteins. Some examples of micropreparative peptide separations are given and capabilities of capillary electromigration techniques to provide important physicochemical characteristics of peptides are demonstrated.

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Section: Electrochromatographymentioning

confidence: 99%

Section: Chiral Analysis and Stereoisomer Separationsmentioning

confidence: 99%

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

2006

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“…In another study, the group employed a chiral biopolymer, viz. poly(L-lysine) hydrobromide as the cationic polymer instead of the achiral PDADMAC [39]. Additionally, poly(L-SULV) was replaced by the anionic dipeptide surfactants poly(sodium N-undecanoyl-L-leucine-alaninate) (poly(L-SULA)) and poly(sodium N-undecanoyl-L-alanine-leucinate) (poly(L-SUAL)), respectively ( Fig.…”

Section: Ot Stationary Phasesmentioning

confidence: 99%

“…Additionally, poly(L-SULV) was replaced by the anionic dipeptide surfactants poly(sodium N-undecanoyl-L-leucine-alaninate) (poly(L-SULA)) and poly(sodium N-undecanoyl-L-alanine-leucinate) (poly(L-SUAL)), respectively ( Fig. 1) [39]. Three binaphthyl derivatives and two b-blockers were used as test analytes and, e.g.…”

Section: Ot Stationary Phasesmentioning

confidence: 99%

Recent accomplishments in the field of enantiomer separation by CEC

Preinerstorfer

Lämmerhofer

2007

Electrophoresis

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Recent accomplishments in the field of enantiomer separation by CECThe present review intends to summarize recent developments in the field of enantioselective separations and analysis by CEC. It covers studies published in English language in common peer-reviewed journals within the period between 2003 and 2006. Both, methods making use of chiral mobile phase additives as well as chiral stationary phases for electrochromatographic enantiomer separations, are reviewed. Achievements that have been made on the various column technologies, such as open-tubular, particle-packed, inorganic, organic and particle-fixed (hybrid-type) monolithic as well as molecularly imprinted polymer phases, are discussed.

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“…These novel coatings allow for facile column fabrication and exceptional separation performance for both chiral and achiral analytes. [23][24][25][26][27] Herein, we report the development of a rapid CE method for studying in vitro post-translational modification-induced protein oligomerization. Capillaries coated with poly (diallyldimethylammonium chloride) (PDADMAC) were used to separate homooligomeric cytochrome c species.…”

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confidence: 99%

Capillary Electrophoretic Screening for the Inhibition of Homocysteine Thiolactone-Induced Protein Oligomerization

et al. 2007

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We report the first demonstration of rapid electrophoretic monitoring of homocysteine thiolactoneinduced protein oligomerization (HTPO), a unique type of post-translational protein modification that may have clinical significance as an indicator of cardiovascular and neurovascular diseases. HTPO of the model protein bovine cytochrome c was initiated in vitro. The relative monomer and aggregate levels of the resultant protein mixtures were determined following separation using capillaries coated with the cationic polymer, poly(diallyldimethylammonium chloride). UV detection provided adequate sensitivity for the monitoring of higher order species, which exist at relatively low concentrations in the protein reaction mixture as compared to the monomeric species. Separations performed under standard injection conditions were optimized on the basis of applied voltage and sample denaturation conditions. Separations performed using short-end injection allowed for more rapid analyses, typically in less than 70 s. Relative errors for run-to-run migration times were less than 0.5%. This novel oligomeric system provides a rapid and straightforward in vitro method to screen therapeutic agents for their ability to inhibit HTPO. Changes in peak area for monomer and aggregate species were used to assess HTPO inhibition as a function of pyridoxal 5-phosphate (PLP) concentration. PLP was shown to effectively inhibit HTPO in vitro. Rapid analysis times of ~1.5 min were achieved for inhibition screening.Hyperhomocysteinemia is a disorder characterized by elevated plasma levels of the naturally occurring amino acid homocysteine (Hcy), which has been identified as an independent risk factor for cardiovascular disease. 1,2 Although the exact function of Hcy in the pathogenesis of cardiovascular disease remains unknown, there is a growing body of evidence that suggests Hcy thiolactone (HTL), the thioester metabolite of Hcy, is a contributing agent. 3-6 HTL is produced in vivo via enzymatic aminoacyl-tRNA synthase pathways at a rate proportional to extracellular Hcy concentration. 7 Thus, it is likely that HTL production is enhanced to some degree in individuals with hyperhomocysteinemia.Post-translational protein modification by HTL involves the site-specific acylation of lysine residues at ε-amino moieties to yield free thiols in the form of protein homocystamide (Scheme 1). 8,9 If left untreated, protein homocystamide can undergo spontaneous in vitro intermolecular disulfide bonding to yield oligomeric species. 10 Protein oligomerization can give rise to a range of adverse physiological affects. For example, oligomeric proteins often exhibit decreased biological activity, decreased solubility, 8 and increased immunogenicity. 11 As one would expect, the extent of physiological dysfunction caused by oligomerization *To whom correspondence should be addressed. strongin@pdx.edu. Tel: (225) In Vitro Protein ModificationProtein reaction mixtures were prepared by dissolving HTL (2.5 mM), and cyt c (10 mg/mL) in pH 7.4, 100 mM so...

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Chiral Separations Using a Polypeptide and Polymeric Dipeptide Surfactant Polyelectrolyte Multilayer Coating in Open-Tubular Capillary Electrochromatography

Cited by 53 publications

References 47 publications

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

Recent accomplishments in the field of enantiomer separation by CEC

Capillary Electrophoretic Screening for the Inhibition of Homocysteine Thiolactone-Induced Protein Oligomerization

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