Mass spectrometry studies of the fragmentation patterns and mechanisms of protonated peptoids.
CID
N-alkylglycine
fragment ion
sequence-controlled polymer
water loss
Journal
Biopolymers
ISSN: 1097-0282
Titre abrégé: Biopolymers
Pays: United States
ID NLM: 0372525
Informations de publication
Date de publication:
Jul 2020
Jul 2020
Historique:
received:
02
01
2020
revised:
02
05
2020
accepted:
04
05
2020
pubmed:
14
6
2020
medline:
7
8
2021
entrez:
14
6
2020
Statut:
ppublish
Résumé
Peptoids belong to a class of sequence-controlled polymers comprising of N-alkylglycine. This study focuses on using tandem mass spectrometry techniques to characterize the fragmentation patterns of a set of singly and doubly protonated peptoids consisting of one basic residue placed at different positions. The singly protonated peptoids fragment by producing predominately high-abundant C-terminal ions called Y-ions and low-abundant N-terminal ions called B-ions. Computational studies suggest that the proton affinity (PA) of the C-terminal fragments is generally higher than that of the N-terminal fragments, and the PA of the former increases as the fragments are elongated. The B-ions are likely formed upon dissociating the proton-activated amide bonds via an oxazolone structure, and the Y-ions are produced subsequently by abstracting a proton from the newly formed B-ions, which is energetically favored. The doubly protonated peptoids prefer to fragment closest to either the N- or the C-terminus and produce corresponding B/Y-ion pairs. The basic residue seems to dictate the preferred fragmentation site, which may be the result of minimizing the repulsion between the two charges. Water and terminal neutral losses are a facile process accompanying the peptoid fragmentation in both charge states. The patterns appear to be highly influenced by the location of the basic residue.
Substances chimiques
N-substituted Glycines
0
Peptoids
0
Protons
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e23358Subventions
Organisme : National Science Foundation
ID : CHE-1301505
Organisme : Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy
ID : DE-AC02-05CH11231
Informations de copyright
© 2020 Wiley Periodicals, Inc.
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