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

Journal of the American Society for Mass Spectrometry
Karnamohit RankaNicolas C Polfer

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.

References

Oct 30, 1998·Journal of the American Society for Mass Spectrometry·K K ThoenH I Kenttämaa
Aug 11, 2000·Journal of the American Society for Mass Spectrometry·R A O'HairC M Hadad
Apr 16, 2003·Accounts of Chemical Research·Stephen J Blanksby, G Barney Ellison
Dec 4, 2003·Journal of the American Society for Mass Spectrometry·Julia Laskin, Jean H Futrell
Jun 24, 2004·Proceedings of the National Academy of Sciences of the United States of America·John E P SykaDonald F Hunt
Feb 8, 2005·Journal of the American Society for Mass Spectrometry·Erik A Syrstad, Frantisek Turecek
Jul 15, 2006·The Journal of Physical Chemistry. a·Monika SobczykJack Simons
Sep 6, 2006·Journal of the American Society for Mass Spectrometry·Gang Hao, Steven S Gross
Nov 23, 2006·Biochimica Et Biophysica Acta·Leann M MikeshDonald F Hunt
Oct 24, 2007·The Journal of Physical Chemistry. a·Jeffrey P MerrickLeo Radom
Dec 15, 2007·Journal of the American Chemical Society·Tony Ly, Ryan R Julian
Feb 26, 2009·Mass Spectrometry Reviews·Nick C Polfer, Jos Oomens
Apr 24, 2009·Journal of the American Chemical Society·Amy L NicelyJames M Lisy
Jan 19, 2010·Journal of the American Chemical Society·Ramakrishnan ParthasarathiKrishnan Raghavachari
Jun 8, 2010·Journal of the American Chemical Society·Tony Ly, Ryan R Julian
Feb 3, 2011·Chemical Society Reviews·Nick C Polfer
Oct 12, 2011·Angewandte Chemie·Bruno BellinaPhilippe Dugourd
Nov 16, 2011·Journal of the American Society for Mass Spectrometry·Claire BrunetLaurent Nahon
Jan 4, 2012·Journal of the American Chemical Society·Vanessa A GallardoHilkka I Kenttämaa
Aug 22, 2012·The Journal of Physical Chemistry. a·Benjamin B KirkRyan R Julian
May 9, 2013·Chemical Reviews·František Tureček, Ryan R Julian
Jul 1, 1990·Journal of the American Society for Mass Spectrometry·E R WilliamsF W McLafferty
May 23, 2014·Journal of the American Society for Mass Spectrometry·Michelle R RobinsonJennifer S Brodbelt
Oct 7, 2016·Journal of the American Society for Mass Spectrometry·Robert PepinFrantišek Tureček
Mar 21, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Michael LesslieVictor Ryzhov
Jul 14, 2017·Journal of the American Society for Mass Spectrometry·Ryan R Julian

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Citations

Jul 2, 2019·Physical Chemistry Chemical Physics : PCCP·Feriel Ben NasrAnne Zehnacker
Jan 18, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Barbara ChiavarinoSimonetta Fornarini
Jun 17, 2020·The Journal of Physical Chemistry. a·Kailin ZhangXianglei Kong
Nov 6, 2021·Rapid Communications in Mass Spectrometry : RCM·Mengying DuXianglei Kong

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