Ultraviolet Action Spectroscopy of Iodine Labeled Peptides and Proteins in the Gas Phase

Kirk, Benjamin B.; Trevitt, Adam J.; Blanksby, Stephen J.; Tao, Yuanqi; Moore, Benjamin; Julian, Ryan R.

doi:10.1021/jp305470j

Cited by 22 publications

(23 citation statements)

References 35 publications

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“…[35][36][37] Kirk et al recently demonstrated the wavelength dependence of iodine atom loss from iodo-tyrosines by photodissociation (PD) action spectroscopy, highlighting the influence of charge state on the efficacy of photoproduct formation. 38 Compared with CID, photodissociation of aryl iodides facilitates the production of radical sites without complications due to isomerisation. 39,40 Strategies that utilise UV radiation and a photolabile radical precursor show promise for peptide characterisation.…”

Section: Introductionmentioning

confidence: 99%

Photodissociation of TEMPO-modified peptides: new approaches to radical-directed dissociation of biomolecules

Marshall

Hansen

Trevitt

et al. 2014

Phys. Chem. Chem. Phys.

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Photodissociation of TEMPO-modified peptides: new approaches to radical-directed dissociation of biomolecules AbstractRadical-directed dissociation of gas phase ions is emerging as a powerful and complementary alternative to traditional tandem mass spectrometric techniques for biomolecular structural analysis. Previous studies have identified that coupling of 2-[(2,2,6,6-tetramethylpiperidin-1-oxyl)methyl]benzoic acid (TEMPO-Bz) to the N-terminus of a peptide introduces a labile oxygen-carbon bond that can be selectively activated upon collisional activation to produce a radical ion. Here we demonstrate that structurally-defined peptide radical ions can also be generated upon UV laser photodissociation of the same TEMPO-Bz derivatives in a linear ion-trap mass spectrometer. When subjected to further mass spectrometric analyses, the radical ions formed by a single laser pulse undergo identical dissociations as those formed by collisional activation of the same precursor ion, and can thus be used to derive molecular structure. Mapping the initial radical formation process as a function of photon energy by photodissociation action spectroscopy reveals that photoproduct formation is selective but occurs only in modest yield across the wavelength range (300-220 nm), with the photoproduct yield maximised between 235 and 225 nm. Based on the analysis of a set of model compounds, structural modifications to the TEMPO-Bz derivative are suggested to optimise radical photoproduct yield. Future development of such probes offers the advantage of increased sensitivity and selectivity for radicaldirected dissociation. AbstractRadical-directed dissociation of gas phase ions is emerging as a powerful and complementary alternative to traditional tandem mass spectrometric techniques for biomolecular structural analysis. Previous studies have identified that coupling of 2-[(2,2,6,6-tetramethylpiperidin-1-oxyl)methyl]benzoic acid (TEMPO-Bz) to the N-terminus of a peptide introduces a labile oxygen-carbon bond that can be selectively activated upon collisional activation to produce a radical ion. Here we demonstrate that structurally-defined peptide radical ions can also be generated upon UV laser photodissociation of the same TEMPO-Bz derivatives in a linear ion-trap mass spectrometer. When subjected to further mass spectrometric analyses, the radical ions formed by a single laser pulse undergo identical dissociations as those formed by collisional activation of the same precursor ion, and can thus be used to derive molecular structure. Mapping the initial radical formation process as a function of photon energy by photodissociation action spectroscopy reveals that photoproduct formation is selective but occurs only in modest yield across the wavelength range (300 -220 nm), with the photoproduct yield maximised between 235 and 225 nm. Based on the analysis of a set of model compounds, structural modifications to the TEMPO-Bz derivative are suggested to optimise radical photoproduct yield. Future development of such probes offers t...

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Section: Introductionmentioning

confidence: 99%

Photodissociation of TEMPO-modified peptides: new approaches to radical-directed dissociation of biomolecules

Marshall

Hansen

Trevitt

et al. 2014

Phys. Chem. Chem. Phys.

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“…For biomolecules, and other molecules with suitably facile bonds, a PD action spectrum can provide rich details about the primary molecular structure, electronic excited states and conformation of ions in the gas-phase [1][2][3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

Hansen

Kirk

Blanksby

et al. 2013

J. Am. Soc. Mass Spectrom.

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. (2013). UV photodissociation action spectroscopy of haloanilinium ions in a linear quadrupole ion trap mass spectrometer. Journal of the American Society for Mass Spectrometry, 24 (6), 932-940. UV photodissociation action spectroscopy of haloanilinium ions in a linear quadrupole ion trap mass spectrometer Abstract UV-vis photodissociation action spectroscopy is becoming increasingly prevalent because of advances in, and commercial availability of, ion trapping technologies and tunable laser sources. This study outlines in detail an instrumental arrangement, combining a commercial ion-trap mass spectrometer and tunable nanosecond pulsed laser source, for performing fully automated photodissociation action spectroscopy on gas-phase ions. The components of the instrumentation are outlined, including the optical and electronic interfacing, in addition to the control software for automating the experiment and performing online analysis of the spectra. To demonstrate the utility of this ensemble, the photodissociation action spectra of 4-chloroanilinium, 4-bromoanilinium, and 4-iodoanilinium cations are presented and discussed. Multiple photoproducts are detected in each case and the photoproduct yields are followed as a function of laser wavelength. It is shown that the wavelength-dependent partitioning of the halide loss, H loss, and NH3 loss channels can be broadly rationalized in terms of the relative carbon-halide bond dissociation energies and processes of energy redistribution. The photodissociation action spectrum of (phenyl)Ag2 + is compared with a literature spectrum as a further benchmark. AbstractUV-Vis photodissociation action spectroscopy is becoming increasingly prevalent due to advances in, and commercial availability of, ion trapping technologies and tunable laser sources. This study outlines in detail an instrumental arrangement, combining a commercial ion-trap mass spectrometer and tunable nanosecond pulsed laser source, for performing fully automated photodissociation action spectroscopy on gas-phase ions. The components of the instrumentation are outlined, including the optical and electronic interfacing, in addition to the control software for automating the experiment and performing online analysis of the spectra. To demonstrate the utility of this ensemble, the photodissociation action spectra of 4-chloroanilinium, 4-bromoanilinium and 4-iodoanilinium cations are presented and discussed. Multiple photoproducts are detected in each case and the photoproduct yields are followed as a function of laser wavelength. It is shown that the wavelength-dependent partitioning of the halide loss, H loss and NH 3 loss channels can be broadly rationalized in terms of the relative carbon-halide bond dissociation energies and processes of energy redistribution. The photodissociation action spectrum of (phenyl)Ag 2 + is compared to a literature spectrum as a further benchmark.3

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“…As mentioned, E(C/T)D techniques yield hydrogen‐rich radical cations of peptides/proteins in multiply protonated forms by adding a low‐energy electron. Hydrogen‐deficient peptide radical cations can also be produced; for example, through photo‐dissociation of protonated peptides derivatized with photo‐labile covalent bonds, under ultraviolet (UV) or vacuum ultraviolet (VUV) irradiation . Peptide dissociation behavior in tert ‐butyl peroxycarbamate–, Vazo 68–, and TEMPO– (2,2,6,6‐tetramethylpiperidine‐1‐oxyl) based FRIPS (free radical–initiated peptide sequencing) MS has been analyzed in both positive‐ and negative‐ion modes for a number of peptides.…”

Section: Common Techniques For Formation Of Peptide Radical Ions In Tmentioning

confidence: 99%

Tautomerization and Dissociation of Molecular Peptide Radical Cations

Mu¹,

Song²,

Siu

et al. 2017

The Chemical Record

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Radical-mediated dissociations of peptide radical cations have intriguing unimolecular gas phase chemistry, with cleavages of almost every bond of the peptide backbone and amino acid side chains in a competitive and apparently "stochastic" manner. Challenges of unraveling mechanistic details are related to complex tautomerizations prior to dissociations. Recent conjunctions of experimental and theoretical investigations have revealed the existence of non-interconvertible isobaric tautomers with a variety of radical-site-specific initial structures, generated from dissociative electron transfer of ternary metal-ligand-peptide complexes. Their reactivity is influenced by the tautomerization barriers, perturbing the nature, location, or number of radical and charge site(s), which also determine the energetics and dynamics of the subsequent radical-mediated dissociatons. The competitive radical- and charge-induced dissociations are extremely dependent on charge density. Charge sequesting can reduce the charge densities on the peptide backbone and hence enhance the flexibility of structural rearrangement. Analysing the structures of precursors, intermediates and products has led to the discovery of many novel radical migration prior to peptide backbone and/or side chain fragmentations. Upon these successes, scientists will be able to build peptide cationic analogues/tautomers having a variety of well-defined radical sites.

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Ultraviolet Action Spectroscopy of Iodine Labeled Peptides and Proteins in the Gas Phase

Cited by 22 publications

References 35 publications

Photodissociation of TEMPO-modified peptides: new approaches to radical-directed dissociation of biomolecules

Photodissociation of TEMPO-modified peptides: new approaches to radical-directed dissociation of biomolecules

UV Photodissociation Action Spectroscopy of Haloanilinium Ions in a Linear Quadrupole Ion Trap Mass Spectrometer

Tautomerization and Dissociation of Molecular Peptide Radical Cations

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