Predicting structural and energetic changes in Met-aromatic motifs on methionine oxidation to the sulfoxide and sulfone

Physical Chemistry Chemical Physics : PCCP
Esam A Orabi, Ann M English

Abstract

Noncovalent interactions between Met and aromatic residues define a common Met-aromatic motif in proteins. Met oxidation to MetOn (n = 1 sulfoxide, n = 2 sulfone) alters protein stability and function. To predict the chemical and physical consequences of such oxidations, we modeled the chemistry and redox properties of MetOn-aromatic complexes in depth for comparison with our Met-aromatic models (E. A. Orabi and A. M. English, J. Phys. Chem. B, 2018, 122, 3760). We describe here ab initio quantum mechanical calculations at the MP2(full)/6-311++G(d,p) level of theory on complexes of MetOn (n = 1, 2; modeled by Me2SO and Me2SO2) with models of the side-chains of Phe (benzene, toluene), Trp (indole, 3-methylindole), Tyr (phenol, 4-methylphenol) and His (imidazole, 4-methylimidazole). Binding energies of the global minimum conformers (-3.4 to -11.9 kcal mol-1) indicate that the gas-phase Me2SOn-aromatics are 40-115% more stable than the Me2S-aromatics. Binding of S between the edge and face of the aromatic ring is favored in most complexes as it accommodates both robust σ- and π-type H-bonding. Interactions involving the σ-holes on the S atoms (σ-holeπar and σ-holeNar/Oar), as well as Sπ interactions in the sulfoxides, contribute t...Continue Reading

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Citations

Jul 31, 2019·Protein Science : a Publication of the Protein Society·Juan C Aledo
Jul 29, 2019·Archives of Biochemistry and Biophysics·David S Weber, Jeffrey J Warren
Mar 2, 2021·Materials Science & Engineering. C, Materials for Biological Applications·Sérgio R S VelosoPaula M T Ferreira
Jul 19, 2021·The Journal of Biological Chemistry·Kiran Sankar Chatterjee, Ranabir Das
May 14, 2020·Journal of the American Society for Mass Spectrometry·Victor Yin, Lars Konermann
Feb 3, 2022·Journal of the American Chemical Society·Katherine I AlbaneseMarcey L Waters

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Methods Mentioned

BETA
NMR

Software Mentioned

Gaussian
MP2
CHARMM36
CHARMM

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