74214-37-2Relevant academic research and scientific papers
Synthesis and Stability of N-Nitrosodipeptides
Challis, Brian C.,Milligan, James R.,Mitchell, Robert C.
, p. 1050 - 1051 (1984)
The synthesis, characterization, and chemical properties of the N-nitroso derivatives of some N-(N-acetylprolyl)-peptides are described.
Decomposition of N-Nitrosopeptides in Strong Acids
Challis, Brian C.,Milligan, Jamie R.,Mitchell, Robert C.
, p. 1595 - 1600 (2007/10/02)
Decomposition of the N-nitrosodipeptides obtained from N-(N'-acetyl-L-prolyl)glycine and N-(N'-acetyl-L-prolyl)-L-alanine in aqueous acid at 25 deg C involves both deamination and denitrosation.Both reactions occur concurrently via different conjugate acid intermediates, with denitrosation being predominant at high acidity.Acidity dependences and inverse solvent deuterium isotope effects suggest that deamination involves rate limiting attack by H2O on an O-conjugate acid, formed in a rapid pre-equilibrium.For denitrosation, H+ transfer to the amide N-atom is considered rate limiting because of the substantial normal solvent deuterium isotope effects and Bunnett ω values in the range -0.1 to -0.5: the N-conjugate acid formed breaks down rapidly to products.Both the kinetics and mechanisms for decomposition of these N-nitrosodipeptides are very similar to those of alicyclic N-nitrosamides.
