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Journal of The American Society for Mass Spectrometry

, Volume 29, Issue 9, pp 1791–1801 | Cite as

Radical Rearrangement Chemistry in Ultraviolet Photodissociation of Iodotyrosine Systems: Insights from Metastable Dissociation, Infrared Ion Spectroscopy, and Reaction Pathway Calculations

  • Karnamohit Ranka
  • Ning Zhao
  • Long Yu
  • John F. Stanton
  • Nicolas C. Polfer
Focus: Application of Photons and Radicals for MS: Research Article

Abstract

We report on the ultraviolet photodissociation (UVPD) chemistry of protonated tyrosine, iodotyrosine, and diiodotyrosine. Distonic loss of the iodine creates a high-energy radical at the aromatic ring that engages in hydrogen/proton rearrangement chemistry. Based on UVPD kinetics measurements, the appearance of this radical is coincident with the UV irradiation pulse (8 ns). Conversely, sequential UVPD product ions exhibit metastable decay on ca. 100 ns timescales. Infrared ion spectroscopy is capable of confirming putative structures of the rearrangement products as proton transfers from the imine and β-carbon hydrogens. Potential energy surfaces for the various reaction pathways indicate that the rearrangement chemistry is highly complex, compatible with a cascade of rearrangements, and that there is no preferred rearrangement pathway even in small molecular systems like these.

Graphical Abstract

Keywords

UVPD Kinetics IRMPD spectroscopy DFT Metastable decay 

Notes

Funding Information

The project was financially supported by the United States National Science Foundation (NSF) under grant number CHE-1403262.

Supplementary material

13361_2018_1959_MOESM1_ESM.pdf (2.1 mb)
ESM 1 (PDF 2141 kb)

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Copyright information

© American Society for Mass Spectrometry 2018

Authors and Affiliations

  • Karnamohit Ranka
    • 1
    • 2
  • Ning Zhao
    • 3
  • Long Yu
    • 3
  • John F. Stanton
    • 1
    • 2
  • Nicolas C. Polfer
    • 3
  1. 1.Quantum Theory Project, Department of ChemistryUniversity of FloridaGainesvilleUSA
  2. 2.Quantum Theory Project, Department of PhysicsUniversity of FloridaGainesvilleUSA
  3. 3.Department of Chemistry and Center for Chemical PhysicsUniversity of FloridaGainesvilleUSA

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