The stereoselective separation of serine containing peptides by zwitterionic ion exchanger type chiral stationary phases and the study of serine racemization mechanisms by isotope exchange and tandem mass spectrometry

Journal of Pharmaceutical and Biomedical Analysis
Roland J Reischl, Wolfgang Lindner

Abstract

The occurrence of d-amino acids (D-AAs) in higher-developed organisms in their free form, and within peptides and proteins, has been investigated with an increasing number of studies. Often the inversion of the stereochemical configuration of an individual amino acid drastically changes its biological activity. Alongside Asn and Asp, Ser is most prone to racemization within peptides. Specific enzymes catalyzing D-Ser generation and breakdown have been described. Hence, the applicability of enantioselective ZWIX(+)(®) and ZWIX(-)(®) chiral stationary phases (CSPs) to peptide separations was assessed and a set of 14 pairs of diastereomeric and enantiomeric Ser and Thr containing di-, tri- and tetra-peptides was chromatographically separated without prior hydrolysis to the individual amino acids. To a certain extent, RP chromatography also enabled the separation of peptide diastereomers. The ZWIX CSPs delivered chromatographic selectivities between 1.04 and 7.23, allowing a change of elution order by switching between the ZWIX(+) and the ZWIX(-) CSP. Coupling these highly selective chromatographic columns with an LTQ-Orbitrap XL™ mass spectrometer and performing high resolution MS(2) measurements enabled us to investigate mechanis...Continue Reading

References

Jan 13, 1992·FEBS Letters·A HashimotoK Takahashi
Nov 26, 1986·Biochemical and Biophysical Research Communications·D S DunlopA Lajtha
Jan 1, 1997·Annual Review of Biochemistry·G Kreil
Sep 22, 1998·FEBS Letters·Z LongK Imai
Nov 11, 1999·Proceedings of the National Academy of Sciences of the United States of America·H WoloskerS H Snyder
Nov 27, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Kenji HamaseKiyoshi Zaitsu
Apr 28, 2005·Analytical and Bioanalytical Chemistry·Christoph Czerwenka, Wolfgang Lindner
Mar 21, 2007·Chemistry : a European Journal·Katsunori KugeNoriko Fujii
Mar 31, 2007·Cellular and Molecular Life Sciences : CMLS·L PollegioniG Molla
Dec 26, 2007·The Journal of Biological Chemistry·Paramjit S BansalPhilip W Kuchel
Jun 20, 2008·The FEBS Journal·Herman WoloskerVeronika N Foltyn
Sep 16, 2008·Analytica Chimica Acta·Bernd O KellerRandy M Whittal
Oct 8, 2008·Analytical and Bioanalytical Chemistry·Sachise EtohKiyoshi Zaitsu
Mar 3, 2010·Cellular and Molecular Life Sciences : CMLS·Loredano Pollegioni, Silvia Sacchi
Jun 22, 2010·Chemistry & Biodiversity·Ohgi TakahashiAkifumi Oda
May 11, 2011·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Yoshitaka GogamiTadao Oikawa
Mar 6, 2012·Journal of Pharmaceutical and Biomedical Analysis·Yurika MiyoshiKenji Hamase
Nov 10, 2012·Protein Science : a Publication of the Protein Society·Michelle Y S HooiRoger J W Truscott
Mar 2, 2013·The FEBS Journal·Brian LyonsRoger J W Truscott
Jun 5, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Céline OllivauxJean-Yves Toullec

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