Journal article

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

Abstract

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..

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