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

J Sep Sci. 2014 Sep;37(18):2447-66. doi: 10.1002/jssc.201400587. Epub 2014 Aug 11.

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.

Keywords: Capillary electrophoresis; Chiral recognition mechanisms; Chiral separation; Hybrid techniques; Peptides.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Chromatography
  • Cyclodextrins / chemistry
  • Electrophoresis, Capillary
  • Molecular Conformation
  • Oligopeptides / chemistry*
  • Oligopeptides / isolation & purification*
  • Stereoisomerism

Substances

  • Cyclodextrins
  • Oligopeptides