Formation, isomerization, and dissociation of alpha-carbon-centered and pi-centered glycylglycyltryptophan radical cations

The Journal of Physical Chemistry. B
Dominic C M NgIvan K Chu

Abstract

Gas phase fragmentations of two isomeric radical cationic tripeptides of glycylglycyltryptophan-[G(*)GW](+) and [GGW](*+)-with well-defined initial radical sites at the alpha-carbon atom and the 3-methylindole ring, respectively, have been studied using collision-induced dissociation (CID), density functional theory (DFT), and Rice-Ramsperger-Kassel-Marcus (RRKM) theory. Substantially different low-energy CID spectra were obtained for these two isomeric GGW structures, suggesting that they did not interconvert on the time scale of these experiments. DFT and RRKM calculations were used to investigate the influence of the kinetics, stabilities, and locations of the radicals on the competition between the isomerization and dissociation channels. The calculated isomerization barrier between the GGW radical cations (>35.4 kcal/mol) was slightly higher than the barrier for competitive dissociation of these species (<30.5 kcal/mol); the corresponding microcanonical rate constants for isomerization obtained from RRKM calculations were all considerably lower than the dissociation rates at all internal energies. Thus, interconversion between the GGW isomers examined in this study cannot compete with their fragmentations.

References

Feb 19, 2000·Journal of Mass Spectrometry : JMS·M J Polce, C Wesdemiotis
Mar 14, 2001·Biochimica Et Biophysica Acta·C L Hawkins, M J Davies
Jul 18, 2001·Journal of the American Chemical Society·C F RodriquezK W Siu
Aug 17, 2001·Journal of the American Society for Mass Spectrometry·P HvelplundT J Jørgensen
Nov 7, 1996·Chemical Reviews·Richard H. HolmEdward I. Solomon
Feb 19, 2002·Chemical Reviews·JoAnne Stubbe, Wilfred A. van Der Donk
Jul 17, 2003·Journal of the American Chemical Society·Nancy LeymariePeter B O'Connor
Feb 18, 2004·Accounts of Chemical Research·Glenn L Millhauser
Apr 23, 2004·Current Opinion in Biotechnology·Roman A Zubarev
Jun 24, 2004·Proceedings of the National Academy of Sciences of the United States of America·John E P SykaDonald F Hunt
Apr 21, 2005·Journal of the American Chemical Society·Christopher K BarlowRichard A J O'Hair
Sep 8, 2005·Journal of the American Chemical Society·Robert HodyssJ L Beauchamp
Mar 1, 2006·Journal of the American Society for Mass Spectrometry·Peter B O'ConnorBogdan A Budnik
Oct 13, 2006·Chemical Communications : Chem Comm·Sheena WeeChristopher J Easton
Oct 13, 2006·Chemical Reviews·Yoshiyasu Matsumoto, Kazuya Watanabe
Jul 20, 2007·Journal of the American Chemical Society·Julia LaskinIvan K Chu
Aug 7, 2007·Analytical Chemistry·Julia LaskinIvan K Chu
Dec 15, 2007·Journal of the American Chemical Society·Tony Ly, Ryan R Julian
May 16, 2008·Journal of the American Chemical Society·Shigeo HayakawaFrantisek Turecek
Dec 31, 2008·Journal of Proteome Research·Qingyu SunRyan R Julian
Feb 17, 2009·Journal of the American Society for Mass Spectrometry·Victor RyzhovRichard A J O'Hair
Mar 4, 2009·Journal of the American Society for Mass Spectrometry·Chi-Kit SiuK W Michael Siu
Apr 25, 2009·Mass Spectrometry Reviews·A C Hopkinson
May 30, 2009·Journal of the American Society for Mass Spectrometry·Liangyi Zhang, James P Reilly
Oct 14, 2008·Journal of Chemical Theory and Computation·Geoffrey P F WoodDavid M Smith

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Citations

Dec 3, 2011·Journal of the American Society for Mass Spectrometry·Tao SongIvan K Chu
Aug 3, 2012·Journal of the American Society for Mass Spectrometry·Anastasia Kalli, Sonja Hess
Jan 31, 2013·Journal of the American Society for Mass Spectrometry·Xing Zhang, Ryan R Julian
Mar 21, 2013·Journal of the American Society for Mass Spectrometry·Andrii PiatkivskyiVictor Ryzhov
May 9, 2013·Chemical Reviews·František Tureček, Ryan R Julian
May 28, 2014·Mass Spectrometry Reviews·Han Bin Oh, Bongjin Moon
Mar 23, 2015·The Journal of Chemical Physics·Bruno BellinaVitaly V Kresin
Jun 27, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xiaoyan MuIvan K Chu
Jun 21, 2017·Physical Chemistry Chemical Physics : PCCP·Xiaoyan MuIvan K Chu
Jan 26, 2012·European Journal of Mass Spectrometry·Ivan K Chu, Julia Laskin
Oct 9, 2014·Physical Chemistry Chemical Physics : PCCP·Cheuk-Kuen LaiIvan K Chu
Feb 18, 2011·Physical Chemistry Chemical Physics : PCCP·Minijie XuIvan K Chu
Apr 18, 2013·Rapid Communications in Mass Spectrometry : RCM·Cheuk-Kuen LaiIvan K Chu

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