Application of TLC, HPLC and GC methods to the study of amino acid and peptide enantiomers: a review

Abstract

Amino acids are very important organic compounds in nature. The biological activity of amino acids depends mainly on their stereoisomeric configuration (d- or l-). Thus, the stereochemical analysis of amino acids and peptides is an important aspect of their characterization. Owing to the increasing role of amino acid configuration in biomedical and pharmaceutical studies, numerous analytical methods have been described in the literature. Among a wide range of analytical techniques available for the steroselective separation of different amino acids, which were obtained from plants or biological samples, chromatographic methods such as thin-layer chromatography, high-performance chromatography and also gas chromatography are very useful. This review presents such systems developed for direct stereoisomeric separation and quantitative determination of amino acid and peptide enantiomers with emphasis on selected literature published during two last decades. Almost all aspects, including sample preparation prior chromatographic analysis, stationary phase, solvent system and detection system, are discussed. New possibilities in chiral amino acid analysis have been opened up by the application of mass spectrometry and infrared detection in thin-layer chromatography and mass spectrometry-selected ion monitoring detection system in gas chromatography. A modern trend in high-performance chromatography is two-dimensional chromatography. These innovations have led to decreased development time and increased amino acid resolution and detectability.

Fine tuning the pH triggers the enantiorecognition of underivatized amino acids by silver nanoparticles: A novel approach based on the focused use of solution equilibria

“…In fact, in spite of the continuous improvement and upgrade of several chromatographic [1] and electrodriven techniques [2] that allow not only the recognition but also the enantioseparation of L-and D-AAs, there is still an increasing demand of simple and ready to use kit for rapid and sensitive detection of D-amino acids. In fact, studies in the last decades [3,4] have shown that D-AAs are widely present in the tissues of higher organisms, including humans, either as products of the vital activities of endogenous flora or during spontaneous racemization of L-AAs in the structure of polypeptides during aging [5,6], as well as endogenous active substances and biomarkers [7,8].…”

Recent development of cationic cyclodextrins for chiral separation

“…Chiral discrimination has attracted considerable attention in academia and industry, especially in biological, pharmaceutical and agrochemical fields [1][2][3]. This interest is attributed to heightened awareness that any compounds of biological and pharmaceutical interest are chiral and their enantiomers often exhibit different bioactivities and biotoxicities.…”

Amino acid analysis using chromatography–mass spectrometry: An inter platform comparison study

“…The chromatographic analysis of AAs has recently been reviewed [7]. Although AA analysis using gas chromatography (GC) with flame-ionization or electron-capture detection has been described, currently GC-MS is becoming more and more wide-spread.…”