Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Abstract

Many chemical and biological processes are controlled by the stereochemistry of small polypeptides (di-, tri-, tetra-, penta-, hexapeptides, etc). The biological importance of peptide stereoisomers is of great value. Therefore, the chiral resolution of peptides is an important issue in biological and medicinal sciences and drug industries. The chiral resolutions of peptide racemates have been discussed with the use of capillary electrophoresis and chromatographic techniques. The various chiral selectors used were polysaccharides, cyclodextrins, Pirkle types, macrocyclic antibiotics, crown ethers, imprinted polymers, etc. The stereochemistry of dipeptides is also discussed. Besides, efforts are made to explain the chiral recognition mechanisms, which will be helpful in understanding existing and developing new stereoselective analyses. Future perspectives of enantiomeric resolution are also predicted. Finally, the review concludes with the demand of enantiomeric resolution of all naturally occurring and synthetic peptides.

Chiral Separations using Miniaturized Techniques: State of the Art and Perspectives

“…However, in the years 1989–1990, some companies started the production of CE apparatus, extending the number of groups working in this field. The work done in CE related to the separation of chiral compounds has been reviewed over the years …”

Simplifying and expanding the screening for peptides <2 kDa by direct urine injection, liquid chromatography, and ion mobility mass spectrometry

“…Methods based on alternative separation strategies (CE, HILIC, etc.) were developed also recently [29][30][31].…”

Enantiomeric resolution and modeling of DL‐alanine‐DL‐tryptophan dipeptide on amylose stationary phase

“…[3][4][5][6][7][8][9][10] Among some methods, high-performance liquid chromatography (HPLC) is thought as the technique of the option for the enantiomeric resolution. [17][18][19][20][21][22][23] Though, only a small amount of articles describe the enantiomeric resolution of the racemates with more than 1 chiral center. [17][18][19][20][21][22][23] Though, only a small amount of articles describe the enantiomeric resolution of the racemates with more than 1 chiral center.…”

“…26 Besides, these control many biological activities of the body. During literature survey, only few articles were found to contain enantiomeric resolution of few dipeptides, 22 but no one describes the enantiomeric resolution of very important aromatic dipeptides DL-alanine-DL-tryptophan ( Figure 1). It is important to write here that dipeptides have 2 chiral centers with 4 enantiomers and hence, a challenge for the enantiomeric resolution.…”