95205-14-4Relevant academic research and scientific papers
α-Bromodiazoacetamides - a new class of diazo compounds for catalyst-free, ambient temperature intramolecular C-H insertion reactions
Kaupang, Asmund,Bonge-Hansen, Tore
supporting information, p. 1407 - 1413 (2013/08/23)
In this work, we introduce a new class of halodiazocarbonyl compounds, α-halodiazoacetamides, which through a metal-free, ambient-temperature thermolysis perform intramolecular C-H insertions to produce α-halo-β-lactams. When carried out with α-bromodiazoacetamides bearing cyclic side chains, the thermolysis reaction affords bicyclic α-halo-β-lactams, in some cases in excellent yields, depending on the ring size and substitution pattern of the cyclic amide side chains.
NITROSATION OF PEPTIDE BONDS. CLEAVAGE OF NITROSATED PEPTIDES BY PYRROLIDINE AND α-AMINO ESTERS
Garcia, Jordi,Gonzalez, Javier,Segura, Ramon,Vilarrasa, Jaume
, p. 3121 - 3128 (2007/10/02)
The reaction of several α-amino acids and peptides (containing Gly, L-Ala, L-Leu, L- or DL-Phe, and/or L- or D-Val) with air-diluted nitrogen oxides has been studied to roughly mimic the N-nitrosation of peptide bonds that the contaminated urban air might produce in pulmonary tissues. Most N-protected α-amino acids give practically quantitative yields of N-nitroso derivatives. N-Protected dipeptides afford either dinitrosated peptides, mixtures of di- and mononitrosated compounds, selectively mononitrosated products, or no reaction at all, depending mainly on steric effects. The same trends are observed for some higher peptides.The (poly)nitrosated peptides, which retain the chirality of the starting materials, have been characterized by 1H and 13C NMR spectroscopy and are cleaved by pyrrolidine and amino esters under mild conditions to give (new) amides or peptides plus diazo derivatives.
