Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers

Peptide modification by a quaternary ammonium group containing a permanent positive charge is a promising method of increasing the ionization efficiency of the analyzed compounds, making ultra-sensitive detection even at the attomolar level possible. Charge-derivatized peptides may undergo both char...

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Autores principales:	Monika Kijewska, Dorota Gąszczyk, Remigiusz Bąchor, Piotr Stefanowicz, Zbigniew Szewczuk
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	derivatization fixed charge tag quaternary ammonium salt mass spectrometry electron-capture dissociation collision induced dissociation Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/fb09efd484c948ca890ac8e3f83dd244
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spelling	oai:doaj.org-article:fb09efd484c948ca890ac8e3f83dd2442021-11-25T18:28:45ZAnalysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers10.3390/molecules262269641420-3049https://doaj.org/article/fb09efd484c948ca890ac8e3f83dd2442021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6964https://doaj.org/toc/1420-3049Peptide modification by a quaternary ammonium group containing a permanent positive charge is a promising method of increasing the ionization efficiency of the analyzed compounds, making ultra-sensitive detection even at the attomolar level possible. Charge-derivatized peptides may undergo both charge remote (ChR) and charge-directed (ChD) fragmentation. A series of model peptide conjugates derivatized with <i>N</i>,<i>N</i>,<i>N</i>-triethyloammonium (TEA), 1-azoniabicyclo[2.2.2]octane (ABCO), 2,4,6-triphenylopyridinium (TPP) and tris(2,4,6-trimetoxyphenylo)phosphonium (TMPP) groups were analyzed by their fragmentation pathways both in collision-induced dissociation (CID) and electron-capture dissociation (ECD) mode. The effect of the fixed-charge tag type and peptide sequence on the fragmentation pathways was investigated. We found that the aspartic acid effect plays a crucial role in the CID fragmentation of TPP and TEA peptide conjugates whereas it was not resolved for the peptides derivatized with the phosphonium group. ECD spectra are mostly dominated by c<sub>n</sub> ions. ECD fragmentation of TMPP-modified peptides results in the formation of intense fragments derived from this fixed-charge tag, which may serve as reporter ion.Monika KijewskaDorota GąszczykRemigiusz BąchorPiotr StefanowiczZbigniew SzewczukMDPI AGarticlederivatizationfixed charge tagquaternary ammonium saltmass spectrometryelectron-capture dissociationcollision induced dissociationOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6964, p 6964 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	derivatization fixed charge tag quaternary ammonium salt mass spectrometry electron-capture dissociation collision induced dissociation Organic chemistry QD241-441
spellingShingle	derivatization fixed charge tag quaternary ammonium salt mass spectrometry electron-capture dissociation collision induced dissociation Organic chemistry QD241-441 Monika Kijewska Dorota Gąszczyk Remigiusz Bąchor Piotr Stefanowicz Zbigniew Szewczuk Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
description	Peptide modification by a quaternary ammonium group containing a permanent positive charge is a promising method of increasing the ionization efficiency of the analyzed compounds, making ultra-sensitive detection even at the attomolar level possible. Charge-derivatized peptides may undergo both charge remote (ChR) and charge-directed (ChD) fragmentation. A series of model peptide conjugates derivatized with <i>N</i>,<i>N</i>,<i>N</i>-triethyloammonium (TEA), 1-azoniabicyclo[2.2.2]octane (ABCO), 2,4,6-triphenylopyridinium (TPP) and tris(2,4,6-trimetoxyphenylo)phosphonium (TMPP) groups were analyzed by their fragmentation pathways both in collision-induced dissociation (CID) and electron-capture dissociation (ECD) mode. The effect of the fixed-charge tag type and peptide sequence on the fragmentation pathways was investigated. We found that the aspartic acid effect plays a crucial role in the CID fragmentation of TPP and TEA peptide conjugates whereas it was not resolved for the peptides derivatized with the phosphonium group. ECD spectra are mostly dominated by c<sub>n</sub> ions. ECD fragmentation of TMPP-modified peptides results in the formation of intense fragments derived from this fixed-charge tag, which may serve as reporter ion.
format	article
author	Monika Kijewska Dorota Gąszczyk Remigiusz Bąchor Piotr Stefanowicz Zbigniew Szewczuk
author_facet	Monika Kijewska Dorota Gąszczyk Remigiusz Bąchor Piotr Stefanowicz Zbigniew Szewczuk
author_sort	Monika Kijewska
title	Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
title_short	Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
title_full	Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
title_fullStr	Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
title_full_unstemmed	Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers
title_sort	analysis of fragmentation pathways of peptide modified with quaternary ammonium and phosphonium group as ionization enhancers
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/fb09efd484c948ca890ac8e3f83dd244
work_keys_str_mv	AT monikakijewska analysisoffragmentationpathwaysofpeptidemodifiedwithquaternaryammoniumandphosphoniumgroupasionizationenhancers AT dorotagaszczyk analysisoffragmentationpathwaysofpeptidemodifiedwithquaternaryammoniumandphosphoniumgroupasionizationenhancers AT remigiuszbachor analysisoffragmentationpathwaysofpeptidemodifiedwithquaternaryammoniumandphosphoniumgroupasionizationenhancers AT piotrstefanowicz analysisoffragmentationpathwaysofpeptidemodifiedwithquaternaryammoniumandphosphoniumgroupasionizationenhancers AT zbigniewszewczuk analysisoffragmentationpathwaysofpeptidemodifiedwithquaternaryammoniumandphosphoniumgroupasionizationenhancers
_version_	1718411113450700800

Analysis of Fragmentation Pathways of Peptide Modified with Quaternary Ammonium and Phosphonium Group as Ionization Enhancers

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