Reaction of Amino Acids, Di- and Tripeptides with the Environmental Oxidant NO3 center dot: A Laser Flash Photolysis and Computational Study
Joses G Nathanael, Amber N Hancock, Uta Wille
CHEMISTRY-AN ASIAN JOURNAL | WILEY-V C H VERLAG GMBH | Published : 2016
Absolute rate coefficients for the reaction between the important environmental free radical oxidant NO3. and a series of N- and C-protected amino acids, di- and tripeptides were determined using 355 nm laser flash photolysis of cerium(IV) ammonium nitrate in the presence of the respective substrates in acetonitrile at 298±1 K. Through combination with computational studies it was revealed that the reaction with acyclic aliphatic amino acids proceeds through hydrogen abstraction from the α-carbon, which is associated with a rate coefficient of about 1.8×106 m-1 s-1 per abstractable hydrogen atom. The considerably faster reaction with phenylalanine [k=(1.1±0.1)×107 m-1 s-1 ] is indicative..View full abstract
Support by the Australian Research Council, The University of Melbourne and the National Computational Infrastructure (NCI) is gratefully acknowledged.