Infrared Multiple-Photon Dissociation Action Spectroscopy of the B Ion from PPG: Evidence of Third Residue Affecting B Fragment Structure

Overview

Journal J Am Soc Mass Spectrom

Specialty Chemistry

Date 2017 Apr 5

PMID 28374317

Citations 4

Authors

John C Poutsma

Jonathan Martens

Jos Oomens

Phillipe Maitre

Vincent Steinmetz

Matthew Bernier

Mengxuan Jia

Vicki Wysocki

Affiliations

Soon will be listed here.

Abstract

Infrared multiple-photon dissociation (IRMPD) action spectroscopy was performed on the b fragment ion from the protonated PPG tripeptide. Comparison of the experimental infrared spectrum with computed spectra for both oxazolone and diketopiperazine structures indicates that the majority of the fragment ion population has an oxazolone structure with the remainder having a diketopiperazine structure. This result is in contrast with a recent study of the IRMPD action spectrum of the PP b fragment ion from PPP, which was found to be nearly 100% diketopiperazine (Martens et al. Int. J. Mass Spectrom. 2015, 377, 179). The diketopiperazine b ion is thermodynamically more stable than the oxazolone but normally requires a trans/cis peptide bond isomerization in the dissociating peptide. Martens et al. showed through IRMPD action spectroscopy that the PPP precursor ion was in a conformation in which the first peptide bond is already in the cis conformation and thus it was energetically favorable to form the thermodynamically-favored diketopiperazine b ion. In the present case, solution-phase NMR spectroscopy and gas-phase IRMPD action spectroscopy show that the PPG precursor ion has its first amide bond in a trans configuration suggesting that the third residue is playing an important role in both the structure of the peptide and the associated ring-closure barriers for oxazolone and diketopiperazine formation. Graphical Abstract ᅟ.

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