Alkali-Metal-Ion-Assisted Hydrogen Atom Transfer in the Homocysteine Radical

Chemistry : a European Journal
Michael LesslieVictor Ryzhov

Abstract

Intramolecular hydrogen atom transfer (HAT) was examined in homocysteine (Hcy) thiyl radical/alkali metal ion complexes in the gas phase by combination of experimental techniques (ion-molecule reactions and infrared multiple photon dissociation spectroscopy) and theoretical calculations. The experimental results unequivocally show that metal ion complexation (as opposed to protonation) of the regiospecifically generated Hcy thiyl radical promotes its rapid isomerisation into an α-carbon radical via HAT. Theoretical calculations were employed to calculate the most probable HAT pathway and found that in alkali metal ion complexes the activation barrier is significantly lower, in full agreement with the experimental data. This is, to our knowledge, the first example of a gas-phase thiyl radical thermal rearrangement into an α-carbon species within the same amino acid residue and is consistent with the solution phase behaviour of Hcy radical.

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Citations

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 11, 2020·Essays in Biochemistry·Christian Schöneich
Dec 5, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Christian Schöneich

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