The Hydrogen–Deuterium Exchange at α-Carbon Atom in<b><i>N,N,N</i></b>-Trialkylglycine Residue: ESI-MS Studies

Wojewska, Dominika; Kluczyk, Alicja; Bąchor, Remigiusz; Stefanowicz, Piotr; Szewczuk, Zbigniew

doi:10.1007/s13361-012-0359-1

Cited by 22 publications

(26 citation statements)

References 13 publications

(16 reference statements)

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“…The ESI‐MS analysis revealed the complete HDX for the oligosarcosine peptide after 10 days at room temperature. Additionally, we observed that in the case of the α ‐C hydrogens of the N,N,N ‐trialkylglycine (betaine) residue in peptides, described by us previously , the H/D exchange occurs within 1 min, which suggests the effect of the quaternary ammonium group on the acidity of the α ‐C hydrogens . We have also found the possibility of such HDX at the α ‐C of the N ‐methyl alanine residue in peptides derivatized by a quaternary ammonium group .…”

Section: Introductionsupporting

confidence: 71%

Convenient preparation of deuterium‐labeled analogs of peptides containing N‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis

Bąchor

Dębowski

Łęgowska

et al. 2015

Journal of Peptide Science

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N-substituted glycines constitute mimics of natural amino acids that are of great interest in the peptide-based drug development. Peptoids-oligo(N-substituted glycines) have been recently demonstrated to be highly active peptidomimetics in biological systems, resistant to proteolytic degradation. We developed a method of the deuterium labeling of peptidomimetics containing N-substituted glycine residues via H/D exchange of their α-carbon hydrogen atoms. The labeling was shown to be easy, inexpensive, and without the use of derivatization reagents or the need for a further purification. The deuterons introduced at the α-carbon atoms do not undergo a back exchange under acidic conditions during liquid chromatography mass spectrometry (LC-MS) analysis. The LC-MS analysis of a mixture of isotopologues revealed a co-elution of deuterated and nondeuterated forms of the peptidomimetics, which may be useful in the quantitative isotope dilution analysis of peptoids and other derivatives of N-substituted glycines.

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Section: Introductionsupporting

confidence: 71%

Convenient preparation of deuterium‐labeled analogs of peptides containing N‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis

Bąchor

Dębowski

Łęgowska

et al. 2015

Journal of Peptide Science

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“…The second procedure was based on the H/D exchange of α-C hydrogens described previously for non-aromatic betaine derivatives ( N,N,N ,-trialkyloglycine)33. This method is limited to peptides containing the quaternary salt at the N-terminal α-amino acids, but cannot occur on the lysine side chain.…”

Section: Resultsmentioning

confidence: 99%

Peptides Labeled with Pyridinium Salts for Sensitive Detection and Sequencing by Electrospray Tandem Mass Spectrometry

Waliczek

Kijewska

Setner

et al. 2016

Sci Rep

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Mass spectrometric analysis of trace amounts of peptides may be problematic due to the insufficient ionization efficiency resulting in limited sensitivity. One of the possible ways to overcome this problem is the application of ionization enhancers. Herein we developed new ionization markers based on 2,4,6-triphenylpyridinium and 2,4,6-trimethylpyridinium salts. Using of inexpensive and commercially available pyrylium salt allows selective derivatization of primary amino groups, especially those sterically unhindered, such as ε-amino group of lysine. The 2,4,6-triphenylpyridinium modified peptides generate in MS/MS experiments an abundant protonated 2,4,6-triphenylpyridinium ion. This fragment is a promising reporter ion for the multiple reactions monitoring (MRM) analysis. In addition, the fixed positive charge of the pyridinium group enhances the ionization efficiency. Other advantages of the proposed ionization enhancers are the simplicity of derivatization of peptides and the possibility of convenient incorporation of isotopic labels into derivatized peptides.

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“…For this purpose, we designed and synthesized a series of oligoproline peptides derivatized with QAS. We performed ESI-MS/MS experiments on M + ions of all the synthesized QAS-peptide derivatives and, with the aid of base-catalyzed hydrogen/deuterium exchange, described by us previously [19], we examined the charge remote fragmentation mechanism, using collision-induced dissociation (CID).…”

Section: Introductionmentioning

confidence: 99%

Gas-Phase Fragmentation of Oligoproline Peptide Ions Lacking Easily Mobilizable Protons

Wieczorek

Kluczyk

Stefanowicz

et al. 2013

J. Am. Soc. Mass Spectrom.

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The fragmentation of peptides containing quaternary ammonium group, but lacking easily mobilizable protons, was examined with the aid of deuterium-labeled analogs and quantum-chemical modeling. The fragmentation of oligoproline containing quaternary ammonium group involves the mobilization of hydrogens localized at α- and γ- or δ-carbon atoms in the pyrrolidine ring of proline. The study of the dissociation pattern highlights the unusual proline residue behavior during MS/MS experiments of peptides.Electronic supplementary materialThe online version of this article (doi:10.1007/s13361-013-0585-1) contains supplementary material, which is available to authorized users.

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The Hydrogen–Deuterium Exchange at α-Carbon Atom inN,N,N-Trialkylglycine Residue: ESI-MS Studies

Cited by 22 publications

References 13 publications

Convenient preparation of deuterium‐labeled analogs of peptides containing N‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis

Convenient preparation of deuterium‐labeled analogs of peptides containing N‐substituted glycines for a stable isotope dilution LC‐MS quantitative analysis

Peptides Labeled with Pyridinium Salts for Sensitive Detection and Sequencing by Electrospray Tandem Mass Spectrometry

Gas-Phase Fragmentation of Oligoproline Peptide Ions Lacking Easily Mobilizable Protons

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