1-(3-Aminopropyl)-3-butylimidazolium bromide for carboxyl group derivatization: potential applications in high sensitivity peptide identification by mass spectrometry

Abstract

The cationic reagent 1-(3-aminopropyl)-3-butylimidazolium bromide (BAPI) was exploited for the derivatization of carboxyl groups on peptides. Nearly 100% derivatization efficiency was achieved with the synthetic peptide RVYVHPI (RI-7). Furthermore, the peptide derivative was stable in a 0.1% TFA/water solution or a 0.1% (v/v) TFA/acetonitrile/water solution for at least one week. The effect of BAPI derivatization on the ionization of the peptide RI-7 was further investigated, and the detection sensitivity was improved >42-fold via matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), thus outperforming the commercial piperazine derivatization approach. Moreover, the charge states of the peptide were largely increased via BAPI derivatization by electrospray ionization (ESI) MS. The results indicate the potential merits of BAPI derivatization for high sensitivity peptide analysis by MS. 1-(3-aminopropyl)-3-butylimidazolium bromide, ionization capacity, peptide, mass spectrometry analysis, derivatization Citation:Qiao X Q, Zhou Y, Hou C Y, et al. 1-(3-Aminopropyl)-3-butylimidazolium bromide for carboxyl group derivatization: potential applications in high sensitivity peptide identification by mass spectrometry. Sci China Life Sci, 2013, 56: 240 -245,

Catch, Modify and Analyze: Methods of Chemoselective Modification of Cysteine-Containing Peptides

“…Several functional groups that can be derivatized easily are present in the peptide structure. These are amino groups at the N -terminus of the peptide chain, or on the lysine side chain, or a carboxyl group at the C -terminus of the peptide, or on the glutamic and aspartic acid side chains [ 39 , 40 ], as well as a thiol group on a cysteine residue. It is also possible to target functional groups that occur as post-translational modifications, such as phosphorylation [ 41 ], and glycosylation [ 42 , 43 , 44 ].…”

Novel pyridinium-based tags: synthesis and characterization for highly efficient analysis of thiol-containing peptides by mass spectrometry

“…5,6 However, the detection sensitivity for proteins/peptides, especially for those with low concentrations and poor ionization efficiency, still can hardly meet the requirements of real sample analysis. Recently, many MS-based tags, such as imidazolium derivatives, [9][10][11] piperazine derivatives, 12-15 guanidine derivatives, 16,17 alkyl tertiary amino or quaternary ammonium derivatives, [18][19][20][21][22][23] phenyl derivatives, [24][25][26] and pyridine derivatives, [27][28][29][30] have been exploited for derivatization of various reactive groups on the peptides with improved ionization efficiency and enhanced detection sensitivity. Recently, many MS-based tags, such as imidazolium derivatives, [9][10][11] piperazine derivatives, 12-15 guanidine derivatives, 16,17 alkyl tertiary amino or quaternary ammonium derivatives, [18][19][20][21][22][23] phenyl derivatives, [24][25][26] and pyridine derivatives, [27][28][29][30] have been exploited for derivatization of various reactive groups on the peptides with improved ionization efficiency and enhanced detection sensitivity.…”

“…7,8 Chemical derivatization is a widely used technique for improving analysis and detection of these proteins and peptides. Recently, many MS-based tags, such as imidazolium derivatives, [9][10][11] piperazine derivatives, [12][13][14][15] guanidine derivatives, 16,17 alkyl tertiary amino or quaternary ammonium derivatives, [18][19][20][21][22][23] phenyl derivatives, [24][25][26] and pyridine derivatives, [27][28][29][30] have been exploited for derivatization of various reactive groups on the peptides with improved ionization efficiency and enhanced detection sensitivity. These tags were systematically summarized in our recently reported review.…”

MALDI Profiling and Applications in Medicine

“…Further advances in the analysis of peptides by MALDI MS have considered whether improvements in sensitivity can be accomplished by chemical derivatisation of the peptides prior to analysis. 1-(3-Aminopropyl)-3-butylimidazolium bromide (BAPI) was utilised to derivatise the C terminal carboxyl groups of peptides prior to analysis and was reported to result in a 42-fold improvement in sensitivity and the derivatisation product was demonstrated to be stable for at least 1 week [ 78 ]. As an alternative, the phosphorylation of the N terminus of the peptides was also investigated as this was selective for the N terminal lysine of tryptic peptides and due to the improved proton affi nity provided by the additional phosphate group attached to the peptides an increase in sensitivity was again reported [ 25 ].…”