Abstract
The selective modification of arginine residues by malondialdehyde (MDA) was used to improve the mass spectrometric analysis of arginine oligomers (Arg(x), x = 4, 6, 7, 8, 9) and an arginine-containing dendrimeric peptide. MDA tagging significantly increased the hydrophobicity of the arginine side-chain and resulted in improved retention in RP HPLC of the oligoarginines using formic acid as mobile phase additive. This avoided the use of TFA to generate sufficient retention, as TFA was shown to lead to a dramatically reduced sensitivity (up to ten-fold for Arg(8) and Arg(9)) as a result of the strong signal suppression by ion pairing with multiple basic residues. MDA modification of Arg oligomers not only resulted in improved detection sensitivity for most of the peptides studied (e. g., more than six-fold for Arg(7)), but also greatly enhanced the quality of MS/MS spectra, in line with previous results for other peptides. Furthermore, MDA modification helped to identify major side products in a sample of a dendrimeric peptide, a class of peptides that is typically difficult to analyze by MS.
References
Feb 17, 2001·Journal of Mass Spectrometry : JMS·V H WysockiL A Breci
Jan 5, 2002·Journal of Chromatography. a·S A GustavssonB Långström
Nov 26, 2002·Journal of Immunological Methods·Antonio VerdolivaVincenzo Manfredi
Sep 16, 2003·The Journal of Biological Chemistry·Luisa BracciPaolo Neri
Sep 25, 2004·Mass Spectrometry Reviews·Béla Paizs, Sándor Suhai
Nov 24, 2004·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Alexander Leitner, Wolfgang Lindner
Sep 1, 2005·Journal of Chromatography. a·Raquel NogueiraWolfgang Lindner
Mar 17, 2006·Journal of Mass Spectrometry : JMS·Alexandra FoettingerWolfgang Lindner
Jun 15, 2006·Analytical Chemistry·Hamid Mirzaei, Fred Regnier
Sep 15, 2006·Proteomics·Alexander Leitner, Wolfgang Lindner
Apr 20, 2007·Chemical Biology & Drug Design·Chiara FalcianiLuisa Bracci
May 5, 2007·Analytical Chemistry·Jennifer L FrahmDavid C Muddimana
Jun 1, 2007·Journal of Mass Spectrometry : JMS·Alexander LeitnerWolfgang Lindner
Citations
Oct 12, 2013·Analytical and Bioanalytical Chemistry·Wenchun XieRichard A Gross
Apr 17, 2009·Journal of Separation Science·Angela SousaJoão A Queiroz
Jun 18, 2011·Expert Review of Proteomics·Christopher M Shuford, David C Muddiman
May 20, 2014·Organic & Biomolecular Chemistry·F TaraballiL Cipolla
Apr 23, 2020·Chemical Reviews·Xiaoran Roger LiuMichael L Gross
Aug 11, 2017·Analytical Chemistry·Dustin C FrostLingjun Li
Jan 10, 2009·Journal of Chromatography. a·Haleem J IssaqTimothy D Veenstra