Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics

Reilly, John M.; Sánchez-Félix, Manuel; Smith, Norman W.

doi:10.1002/chir.10264

Cited by 10 publications

(10 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Most important representatives of peptide chiral selectors are macrocyclic glycopeptides, vancomycin, ristocetin and teicoplanin, used for a broad class of chiral separations both in electromigration and in chromatographic techniques [293]. 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%

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

2006

View full text Add to dashboard Cite

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.

show abstract

Section: Chiral Analysis and Stereoisomer Separationsmentioning

confidence: 99%

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

2006

View full text Add to dashboard Cite

show abstract

“…Chiral analysis has previously been achieved using various chiral selectors such as cyclodextrins (CDs) [6][7][8][9][10], antibiotics [11][12][13][14], and crown ethers [15][16][17][18]. However, despite good chiral recognition ability, these chiral selectors have several limitations resulting from low solubility, high cost, and difficult synthetic procedures.…”

Section: Introductionmentioning

confidence: 99%

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

et al. 2007

View full text Add to dashboard Cite

Novel fluorescent chiral molecular micelles (FCMMs) were synthesized, characterized, and employed as chiral selectors for enantiomeric recognition of non-fluorescent chiral molecules using steady state fluorescence spectroscopy. The sensitivity of the fluorescence technique allowed for investigation of low concentrations of chiral selector (3.0×10 −5 M) and analyte (5.0×10 −6 M) to be used in these studies. The chiral interactions of glucose, tartaric acid, and serine in the presence of, and poly(sodium N-undecanoyl-L-phenylalininate) [poly-SUF] were based on diastereomeric complex formation. Poly-L-SUW had a significant fluorescence emission spectral difference as compared to poly-L-SUY and poly-L-SUF for the enantiomeric recognition of glucose, tartaric acid, and serine. Studies with the hydrophobic molecule α-pinene suggested that poly-L-SUY and poly-L-SUF had better chiral discrimination ability for hydrophobic analytes as compared to hydrophilic analytes. Partial-least-squares regression modeling (PLS-1) was used to correlate changes in the fluorescence emission spectra of poly-L-SUW due to varying enantiomeric compositions of glucose, tartaric acid, and serine for a set of calibration samples. Validation of the calibration regression models was determined by use of a set of independently prepared samples of the same concentration of chiral selector and analyte with varying enantiomeric composition. Prediction ability was evaluated by use of the root-mean-square percent relative error (RMS%RE) and was found to range from 2.04 to 4.06%.

show abstract

“…One ring 2 chlorine substituent of I closely inserted into the cavity of the other molecule of the dimer [22]. Several examples of enantioresolution with vanco mycin-type chiral selectors have shown that dimerization may also increase enantioresolution for dansyl-amino acids [18,19,44]. The higher the dimerization constant, the higher the dimer concentration and thus the higher the enantioselectivity will be.…”

Section: Comparison Of the Enantioresolution R S Between I And Iiimentioning

confidence: 96%

Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis

et al. 2006

View full text Add to dashboard Cite

The vancomycin-type glycopeptide antibiotic balhimycin (I) and its dehaloanalogue dechlorobalhimycin (III), which is characterized by the total substitution of the two chlorine atoms of I by hydrogen, were employed as chiral selectors for the enantioresolution of 11 racemic dansyl amino acids and six 2-arylpropionic acid nonsteroidal anti-inflammatory racemic drugs by CE. The observed enantioresolution capability of I for all test analytes is clearly higher than that observed for III. This result suggests that chlorine substituents of I played a major role in the enantioresolution of these test analytes. A dimerization-based mechanism is proposed in order to explain this phenomenon. The two chlorine substituents of each monomer, which mutually penetrate into the cavity of the adjacent molecule of the dimer, are assumed to promote dimerization and as a consequence also enantioresolution.

show abstract

Link between biological signaling and increased enantioseparations of acids using glycopeptide antibiotics

Cited by 10 publications

References 19 publications

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

Recent developments in capillary electrophoresis and capillary electrochromatography of peptides

Determination of Enantiomeric Compositions of Analytes Using Novel Fluorescent Chiral Molecular Micelles and Steady State Fluorescence Measurements

Highlighting the role of the chlorine substituents in the glycopeptide antibiotic balhimycin for chiral recognition in capillary electrophoresis

Contact Info

Product

Resources

About