PMID- 24375876
OWN - NLM
STAT- MEDLINE
DCOM- 20140707
LR  - 20131230
IS  - 1097-0231 (Electronic)
IS  - 0951-4198 (Linking)
VI  - 28
IP  - 3
DP  - 2014 Feb 15
TI  - Development of a novel imidazolium-based aromatic quaternary ammonium tag: 
      synthesis and application to the efficient analysis of cysteinyl-peptides by mass 
      spectrometry.
PG  - 256-64
LID - 10.1002/rcm.6785 [doi]
AB  - RATIONALE: Chemical derivatization is a very promising technique for improving 
      analysis of peptides by mass spectrometry (MS). In this study, a novel kind of 
      imidazolium-based aromatic quaternary ammonium tag, 
      1-[3-[(2-iodo-1-oxoethyl)amino]propyl]-3-butylimidazolium bromide (IPBI), 
      designed with strong gas-phase basicity and a permanent positive charge, was 
      firstly synthesized and further used for derivatization of cysteinyl-peptides 
      with improved ionization efficiency and higher charge states. METHODS: Both the 
      model peptides and tryptic digests of proteins were used to evaluate the effect 
      of IPBI derivatization on the MS performance of the derivatized peptides, and the 
      results were further compared with the commonly used iodoacetamide (IAA) tag. 
      Matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF)-MS and 
      electrospray ionization (ESI)-MS were used to evaluate the ionization efficiency 
      and charge states of the derivatized peptides. RESULTS: With model peptides as 
      samples, a nearly 100% derivatization efficiency and superior stability were 
      achieved via IPBI derivatization. By further analysis of both standard peptides 
      and tryptic protein digests, the ionization efficiency and charge states of 
      IPBI-derivatized peptides could be remarkably improved. For example, for protein 
      bovine serum albumin, compared with the commercial available IAA tag, the 
      identification efficiency of cysteinyl-peptides was increased about 67% by 
      combining with IPBI derivatization. CONCLUSIONS: The results indicated that the 
      novel tag is an effective derivatization reagent for cysteinyl-peptide 
      identification. We hope it could be further used for high-efficiency 
      cysteinyl-peptide identification in proteome research, especially those with low 
      abundance and poor ionization efficiency.
CI  - Copyright (c) 2013 John Wiley & Sons, Ltd.
FAU - Qiao, Xiaoqiang
AU  - Qiao X
AD  - Key Laboratory of Pharmaceutical Quality Control of Hebei Province & College of 
      Pharmaceutical Sciences, Hebei University, Baoding, 071002, China.
FAU - Wang, Rui
AU  - Wang R
FAU - Yan, Hongyuan
AU  - Yan H
FAU - Wang, Tao
AU  - Wang T
FAU - Zhao, Qun
AU  - Zhao Q
FAU - Zhang, Lihua
AU  - Zhang L
FAU - Zhang, Yukui
AU  - Zhang Y
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Rapid Commun Mass Spectrom
JT  - Rapid communications in mass spectrometry : RCM
JID - 8802365
RN  - 0 (Imidazoles)
RN  - 0 (Peptide Fragments)
RN  - 0 (Proteins)
RN  - 0 (Quaternary Ammonium Compounds)
RN  - 7GBN705NH1 (imidazole)
RN  - K848JZ4886 (Cysteine)
SB  - IM
MH  - Animals
MH  - Cattle
MH  - Cysteine/chemistry
MH  - Imidazoles/*chemistry
MH  - Molecular Probe Techniques
MH  - Peptide Fragments/*analysis/chemistry
MH  - Proteins/analysis/chemistry
MH  - Quaternary Ammonium Compounds/*chemistry
MH  - Tandem Mass Spectrometry/*methods
EDAT- 2014/01/01 06:00
MHDA- 2014/07/08 06:00
CRDT- 2013/12/31 06:00
PHST- 2013/09/21 00:00 [received]
PHST- 2013/10/30 00:00 [revised]
PHST- 2013/11/12 00:00 [accepted]
PHST- 2013/12/31 06:00 [entrez]
PHST- 2014/01/01 06:00 [pubmed]
PHST- 2014/07/08 06:00 [medline]
AID - 10.1002/rcm.6785 [doi]
PST - ppublish
SO  - Rapid Commun Mass Spectrom. 2014 Feb 15;28(3):256-64. doi: 10.1002/rcm.6785.