32483-15-1Relevant articles and documents
Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies
Nathanael, Joses G.,Wille, Uta
, p. 3405 - 3418 (2019/03/11)
Kinetic and computational data reveal a complex behavior of the important environmental free radical oxidant NO3? in its reactions with aliphatic amino acids and di- and tripeptides, suggesting that attack at the amide N-H bond in the peptide backbone is a highly viable pathway, which proceeds through a proton-coupled electron transfer (PCET) mechanism with a rate coefficient of about 1 × 106 M-1 s-1 in acetonitrile. Similar rate coefficients were determined for hydrogen abstraction from the α-carbon and from tertiary C-H bonds in the side chain. The obtained rate coefficients for the reaction of NO3? with aliphatic di- and tripeptides suggest that attack occurs at all of these sites in each individual amino acid residue, which makes aliphatic peptide sequences highly vulnerable to NO3?-induced oxidative damage. No evidence for amide neighboring group effects, which have previously been found to facilitate radical-induced side-chain damage in phenylalanine, was found for the reaction of NO3? with side chains in aliphatic peptides.
Aqueous Solutions Containing Amino Acids and Peptides. Part 16. --Solute-Solute Interactions in Solutions Containing some N-Acetyl-N'-methylamino Acid Amides
Blackburn, G. Michael,Lilley, Terence H.,Milburn, Peter J.
, p. 2191 - 2206 (2007/10/02)
The energetics of the interactions occuring between some N-acetyl-N'-methylamino acid amides in aqueous solutions at 25 deg C have been investigated.Osmotic coefficients and enthalpies of dilution have been obtained for single-component and two-component
