Reactions of deprotonated tyrosine and tryptophan with electronically excited singlet molecular oxygen (a1Δ(g)): a guided-ion-beam scattering, statistical modeling, and trajectory study

The Journal of Physical Chemistry. B
Fangwei LiuJianbo Liu

Abstract

The reactions of deprotonated tyrosine ([Tyr-H](-)) and tryptophan ([Trp-H](-)) with the lowest electronically excited state of molecular oxygen O(2)[a(1)Δ(g)] have been studied in the gas phase, including the measurement of the effects of collision energy (E(col)) on reaction cross sections over a center-of-mass E(col) range from 0.05 to 1.0 eV. [Tyr-H](-) and [Trp-H](-) were generated using electrospray ionization, and both have a pure carboxylate anion structure in the gas phase. Density functional theory calculations and RRKM modeling were used to examine properties of various complexes, transition states, and products that might be important along the reaction coordinate. It was found that deprotonation of Tyr and Trp results in a large effect on their (1)O(2)-mediated oxidation. For [Tyr-H](-), the reaction corresponds to the formation of a hydroperoxide intermediate, followed by intramolecular H transfer and subsequent dissociation to product ion 4-(2-aminovinyl)phenolate, and neutral H(2)O(2) and CO(2). Despite that the reaction is 1.83 eV exothermic, the reaction cross section shows a threshold-like behavior at low E(col) and increases with increasing E(col), suggesting that the reaction bears an activation barrier abo...Continue Reading

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Citations

Jan 28, 2016·Chemistry : a European Journal·Wenchao Lu, Jianbo Liu
Oct 28, 2019·Journal of Mass Spectrometry : JMS·Emerson Finco MarquesPaolo Di Mascio
Aug 13, 2017·Journal of Mass Spectrometry : JMS·Emerson Finco MarquesPaolo Di Mascio
May 23, 2015·The Journal of Physical Chemistry. B·Fangwei Liu, Jianbo Liu
Mar 9, 2019·The Journal of Physical Chemistry. a·Nicole EyetVeronica M Bierbaum

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