Comparative DFT study to determine if α-oxoaldehydes are precursors for pentosidine formation

The Journal of Physical Chemistry. a
Rasoul NasiriAli Akbar Moosavi-Movahedi

Abstract

We report a comprehensive density functional theory (DFT) study of the mechanism of pentosidine formation. This work is a continuation of our earlier studies in which we proposed pathways for formation of glucosepane (J. Mol. Model. 2011, pp 1-15, DOI 10.1007/s00894-011-1161-x), GODIC (glyoxal-derived imidazolium cross-link), and MODIC (methyl glyoxal-derived imidazolium cross-link; J. Phys. Chem. 2011, 115, pp 13542-13555). Here we show that formation of pentosidine via reaction of α-oxoaldehydes with lysine and arginine in aqueous solution is possible thermodynamically and kinetically, in good agreement with the available experimental evidence. Five pathways, A-E, were characterized, as in our previous GODIC and MODIC work. In pathways A and B, a Schiff base is first formed from lysine and methyl glyoxal (MGO), and this is followed by addition of arginine and glyoxal (GO). By contrast, in pathways C, D, and E, addition of arginine to MGO occurs first, resulting in the formation of imidazolone, which then reacts with lysine and GO to give pentosidine. Our calculations show that the reaction process is highly exergonic and that the three pathways A, C, and E are competitive. These results serve to underline the potentially impo...Continue Reading

References

Sep 4, 1998·Journal of the American Society of Nephrology : JASN·S SugiyamaK Kurokawa
Dec 16, 1998·Journal of the American Society of Nephrology : JASN·T MiyataC van Ypersele de Strihou
Dec 22, 1999·The International Journal of Biochemistry & Cell Biology·J E LitchfieldJ W Baynes
Apr 1, 2003·Journal of Computational Chemistry·Maurizio CossiVincenzo Barone
Jul 23, 2005·Annals of the New York Academy of Sciences·Paul J Thornalley
Jul 23, 2005·Annals of the New York Academy of Sciences·A LapollaP Traldi
Nov 8, 2008·Physical Chemistry Chemical Physics : PCCP·Jeng-Da Chai, Martin Head-Gordon
Mar 17, 2010·Medicina clínica·Sonia MoralesManuel Muñoz-Torres
Oct 23, 2010·Multiple Sclerosis : Clinical and Laboratory Research·Zohara SternbergFrederick Munschauer
Oct 6, 2011·The Journal of Physical Chemistry. a·Rasoul NasiriAli Akbar Moosavi-Movahedi

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Citations

Apr 4, 2017·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Ahmed S Abo Dena, Sara A Abdel Gaber
Feb 26, 2015·Journal of the American Chemical Society·R Erik Plata, Daniel A Singleton

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