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High performance liquid chromatographic separation of dipeptide and tripeptide enantiomers using a chiral crown ether stationary phase
Author(s) -
Conrad Uwe,
Chankvetadze Bezhan,
Scriba Gerhard K. E.
Publication year - 2005
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.200500193
Subject(s) - tripeptide , enantiomer , chemistry , dipeptide , elution , chromatography , crown ether , ether , resolution (logic) , methanol , ammonium acetate , high performance liquid chromatography , sulfuric acid , amino acid , organic chemistry , ion , biochemistry , artificial intelligence , computer science
A chiral stationary phase (CSP) based on (–)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid was evaluated for the direct resolution of the enantiomers of dipeptides and tripeptides. The type and concentration of the acid and the methanol content were optimized with regard to retention time and resolution using Ala‐Phe as model peptide. A mobile phase consisting of 10 mM sulfuric acid in 70% aqueous methanol was applied to the separation of a set of 16 structurally diverse dipeptides and tripeptides. Generally, the configuration of the amino acid at the N‐terminus determined the enantiomer elution order. With a few exceptions the LL ‐ and LD ‐enantiomers interacted stronger with the CSP compared to the corresponding DD ‐ or DL ‐enantiomers. The experimental conditions also allowed the simultaneous separation of all four stereoisomers of Ala‐Phe. Addition of ammonium sulfate generally reduced retention times and enantiomer resolution. Addition of triethylamine as modifier led to an overall increase of the retention times while the resolution did not show a general trend, increasing in the case of Ala‐Ala but decreasing in the case of Ala‐Phe.