Liquid chromatographic-mass spectrometric separation of oligoalanine peptide stereoisomers: influence of absolute configuration on enantioselectivity and two-dimensional separation of diastereomers and enantiomers

Journal of Chromatography. a
Christoph CzerwenkaW Lindner

Abstract

This contribution describes the chromatographic separation of peptide stereoisomers. Thereby, one focus is laid on the influence of the absolute configurations of peptide enantiomer pairs on their enantioselective separation. Three different N-terminal protecting groups and three different chiral stationary phases (CSPs) based on cinchona alkaloid derivatives were employed and oligoalanine di-, tri- and tetra-peptides were used as model set. The absolute configurations of the individual enantiomeric pairs were found to profoundly influence both the elution order and the enantioselectivity. The stereoselective molecular recognition mechanism was observed to be dependent on the combination of configuration and the chosen protecting group and CSP. As the CSPs on their own exhibited insufficient diastereoselectivity, a two-dimensional liquid chromatography-mass spectrometry (LC-MS) system was developed for the separation of both diastereomers and enantiomers of peptides in the second part of this study. Diastereomers were separated by reversed phase (RP) and the resulting enantiomeric pair fractions were transferred to a CSP for enantioseparation. All eight stereoisomers of a tripeptide (Ala-Ala-Ala) and 9 out of 10 stereoisomers o...Continue Reading

Citations

Apr 28, 2005·Analytical and Bioanalytical Chemistry·Christoph Czerwenka, Wolfgang Lindner
May 22, 2010·Bioanalytical Reviews·Lu BaiJonathan V Sweedler
Sep 5, 2012·Journal of Separation Science·Ramisetti Nageswara RaoBompelli Sravan Kumar
Apr 21, 2010·Journal of Separation Science·Chun LinZiyuan Guo
Aug 24, 2005·Journal of Colloid and Interface Science·Juraj BujdákBernd M Rode
May 10, 2006·Chirality·Ralf PätzoldHans Brückner
Jul 22, 2014·Journal of Separation Science·Imran AliAlexander Chudinov
Nov 9, 2004·Journal of Mass Spectrometry : JMS

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