Chiral separation with dipeptide-terminated polymeric surfactants: The effect of an extra heteroatom on the polar head group

Haynes, Judson L.; Billiot, Eugene; Yarabe, H. Hyacinthe; Warner, Isiah M.; Shamsi, Shahab A.

doi:10.1002/(sici)1522-2683(20000501)21:8<1597::aid-elps1597>3.0.co;2-l

Cited by 29 publications

(3 citation statements)

References 20 publications

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“…In fact, the resolution of the atropisomers of either BN or some of its derivatives has been achieved by means of micellar electrokinetic chromatography (MEKC) with bile salts, chiral surfactants, g-cyclodextrin (g-CD) sulfobutyl ethers, calixarenes or combined chiral polymer/ g-CD micelles in the running buffer [7][8][9][10][11][12][13][14][15]. On the other hand, a few studies with capillary zone electrophoresis (CZE) proved its effectiveness in resolving BN atropisomers with the aid of both native and derivatized CDs [15,16], monosaccharides, diethylaminomethyldextran or aminoglycosidic antibiotics in the running buffer [17,18].…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin-assisted capillary electrophoretic resolution of 1,1′-bi-2-naphthol atropisomers

Zerbinati

Trotta

2001

Electrophoresis

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Native beta- and gamma-cyclodextrin (CD), neutral beta-CD derivatives and ethylcarbonate derivatives of beta- and gamma-CD were used as stereoselective additives for CD-capillary zone electrophoresis (CZE) resolution of atropisomers of 1,1'-bi-(2-naphthol) (BN). CZE experiments at variable CD concentration allowed calculating binding constants from electrophoretic mobility data, corrected for electroosmotic flow (EOF) and running buffer viscosity variations. The CDs were chosen on the basis of geometric examination of molecular models of BN and CDs that suggested the possibility of inclusion complexes formation. Optimum concentrations, with aqueous 25 mM phosphate running buffer at pH 10.5, 36 cm x 50 microm capillary and 10 kV applied potential, were 3.6, 3.9, 2.1, 2.2, 1.9 mM for beta-CD, gamma-CD, ethylcarbonate-beta-CD, methyl-beta-CD and hydroxypropyl-beta-CD, respectively.

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Section: Introductionmentioning

confidence: 99%

Cyclodextrin-assisted capillary electrophoretic resolution of 1,1′-bi-2-naphthol atropisomers

Zerbinati

Trotta

2001

Electrophoresis

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“…Peptides are not only the subject of CE chiral separations but they are used also as chiral selectors for separation of other classes of enantiomeric compounds. Dipeptide polymerized surfactants [218][219][220][221][222][223] and cyclohexapeptides obtained by combinatorial synthesis [224] are other examples of peptide-based chiral selectors. Dipeptide polymerized surfactants [218][219][220][221][222][223] and cyclohexapeptides obtained by combinatorial synthesis [224] are other examples of peptide-based chiral selectors.…”

Section: Chiral Analysis and Stereoisomer Separationmentioning

confidence: 99%

Recent advances in capillary electrophoresis of peptides

Kašička

2001

Electrophoresis

100

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The article gives a comprehensive review on the recent developments in the applications of high-performance capillary electromigration methods, including 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, and covers the methodological aspects of capillary electroseparations of peptides, such as strategy and rules for the rational selection of separation mode and experimental conditions, sample treatment, suppression of peptide adsorption to the inner capillary wall, 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 for determination of purity, determination in biomatrices, monitoring of physical and chemical changes and enzymatic conversions, 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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“…In addition, it is well-known that hydrogen bonds play very important roles in biological systems and that most of the molecules of importance to living systems are chiral, e.g., amino acids, sugars, proteins, and nucleic acids. Actually, chiral surfactants are specialty molecules to be used in enantioseparation of pharmaceutical molecules and in stereoselective synthesis. − Chiral vesicles are a special class of supramolecules that allow them to be used as enantiosensitive analytical reagents. , One of the important effects of chirality in surfactant systems is the “chiral bilayer effect” where the hydrophobic aggregates have an enhanced lifetime. Chiral vesicles are ideal candidates to be used as carriers for chiral drug molecules.…”

Section: Introductionmentioning

confidence: 99%

Spontaneous Formation of Vesicles by Self-Assembly of Nicotinyl Amino Acid Amphiphiles: Application as “Turn-On” Fluorescent Sensors for the Selective Detection of Trace-Level Hg(II) in Water

Roy

2016

Ind. Eng. Chem. Res.

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In this paper, the three nicotinic acid-based amphiphiles, sodium 6-dodecylnicotinic glycinate, sodium 6-dodecylnicotinic alaninate, and sodium 6-dodecylnicotinic valinate, were synthesized, and the effect of the headgroup on the self-assembly properties was investigated. The interfacial properties were determined by tensiometry measurement. A steady-state fluorescence technique was used to investigate the microenvironment of the self-assemblies. The amphiphiles form vesicles in water, and the size of the aggregates decreases with increase in the hydrophobicity of the headgroup. Gel permeation chromatography and kinetic studies were performed to establish the entrapping and releasing properties of the vesicles. The arrangement of the hydrocarbon chains in the lamella was examined by X-ray diffraction study. Circular dichroism spectra suggested formation of chiral structure through aggregation of the chiral amphiphiles. It has been demonstrated that the amphiphiles have the feasibility to be developed for use as sensors for rapid determination of Hg2+ ions in aqueous biological and environmental samples.

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Chiral separation with dipeptide-terminated polymeric surfactants: The effect of an extra heteroatom on the polar head group

Cited by 29 publications

References 20 publications

Cyclodextrin-assisted capillary electrophoretic resolution of 1,1′-bi-2-naphthol atropisomers

Cyclodextrin-assisted capillary electrophoretic resolution of 1,1′-bi-2-naphthol atropisomers

Recent advances in capillary electrophoresis of peptides

Spontaneous Formation of Vesicles by Self-Assembly of Nicotinyl Amino Acid Amphiphiles: Application as “Turn-On” Fluorescent Sensors for the Selective Detection of Trace-Level Hg(II) in Water

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