Derivatization of peptides as quaternary ammonium salts for sensitive detection by ESI-MS

被引:37
作者
Cydzik, Marzena [1 ]
Rudowska, Magdalena [1 ]
Stefanowicz, Piotr [1 ]
Szewczuk, Zbigniew [1 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
关键词
quaternary ammonium salts; derivatization of peptides; peptide fragmentation; sequencing; TANDEM MASS-SPECTROMETRY; COLLISION-INDUCED DISSOCIATION; TERMINAL DERIVATIZATION; CHARGE DERIVATIZATION; PROTONATED PEPTIDES; AMADORI PRODUCTS; FRAGMENTATION; DERIVATIVES; IONS;
D O I
10.1002/psc.1342
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of model peptides in the form of quaternary ammonium salts at the N-terminus was efficiently prepared by the solid-phase synthesis. Tandem mass spectrometric analysis of the peptide quaternary ammonium derivatives was shown to provide sequence confirmation and enhanced detection. We designed the 2-(1,4-diazabicyclo[2.2.2] octylammonium) acetyl quaternary ammonium group which does not suffer from neutral losses during MS/MS experiments. The presented quaternization of 1,4-diazabicyclo[2.2.2] octane (DABCO) by iodoacetylated peptides is relatively easy and compatible with standard solid-phase peptide synthesis. This methodology offers a novel sensitive approach to analyze peptides and other compounds. Copyright (C) 2011 European Peptide Society and John Wiley & Sons, Ltd.
引用
收藏
页码:445 / 453
页数:9
相关论文
共 37 条
[1]   CHARGE-REMOTE FRAGMENTATIONS - ANALYTICAL APPLICATIONS AND FUNDAMENTAL-STUDIES [J].
ADAMS, J .
MASS SPECTROMETRY REVIEWS, 1990, 9 (02) :141-186
[2]   Nucleophilicities and Lewis basicities of imidazoles, benzimidazoles, and benzotriazoles [J].
Baidya, Mahiuddin ;
Brotzel, Frank ;
Mayr, Herbert .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (08) :1929-1935
[3]   Amino-terminal dimerization of peptides on the solid support. Synthesis and biological activity of the immunosuppressive HLA-DR fragments linked by poly(ethylene glycol)s [J].
Biernat, Monika ;
Stefanowicz, Piotr ;
Zimecki, Michal ;
Szewczuk, Zbigniew .
BIOCONJUGATE CHEMISTRY, 2006, 17 (05) :1116-1124
[4]   Synthesis and analysis of potential prodrugs of coenzyme A analogues for the inhibition of the histone acetyltransferase p300 [J].
Cebrat, M ;
Kim, CM ;
Thompson, PR ;
Daugherty, M ;
Cole, PA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (15) :3307-3313
[5]   Improving de novo sequencing of peptides using a charged tag and C-terminal digestion [J].
Chen, Weibin ;
Lee, Peter J. ;
Shion, Henry ;
Ellor, Nicholas ;
Gebler, John C. .
ANALYTICAL CHEMISTRY, 2007, 79 (04) :1583-1590
[6]  
Cheng CF, 2000, MASS SPECTROM REV, V19, P398
[7]   Review - Mass spectrometry and protein analysis [J].
Domon, B ;
Aebersold, R .
SCIENCE, 2006, 312 (5771) :212-217
[8]   GENERAL-METHOD FOR RAPID SYNTHESIS OF MULTICOMPONENT PEPTIDE MIXTURES [J].
FURKA, A ;
SEBESTYEN, F ;
ASGEDOM, M ;
DIBO, G .
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (06) :487-493
[9]   A picomole-scale method for charge derivatization of peptides for sequence analysis by mass spectrometry [J].
Huang, ZH ;
Wu, J ;
Roth, KDW ;
Yang, Y ;
Gage, DA ;
Watson, JT .
ANALYTICAL CHEMISTRY, 1997, 69 (02) :137-144
[10]   COLLISION-INDUCED FRAGMENTATION OF (M+H)+IONS OF PEPTIDES - SIDE-CHAIN SPECIFIC SEQUENCE IONS [J].
JOHNSON, RS ;
MARTIN, SA ;
BIEMANN, K .
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, 1988, 86 :137-154