Mutagenicity of (azaserine) and 6-diazo-5-oxo-l-norleucine (DON) in a soybean test system

Copper carbenes alkylate guanine chemoselectively through a substrate directed reaction

“…50 , 51 In addition, since diazotized peptides are the likely source of these alkylation adducts, 26 , 50 it is important to understand whether adducts bearing amides are also effectively repaired. Bacteria also produce diazo peptide natural products that may alkylate DNA, 52 , 53 adding additional impetus to understand the repair of amide adducts. Thus, we tested whether a DNA 9-mer modified with a cyclohexyl carboxymethylamide (see Table 2 , entry 6), was a substrate for hAGT (see Fig.…”

Properties and reactivity of nucleic acids relevant to epigenomics, transcriptomics, and therapeutics

“…Although the primary mode-of-action of -diazo carbonyl compounds is believed to be as glutamine antimetabolites, their mutagenic activity may suggest DNA as a secondary target. [92][93][94] In fact diazoacetate formation is believed to occur frequently in humans as a result of nitrosation of the N-terminus of peptides or glycine itself (found especially in persons with high red meat or cured meat diets). 95 DNA examined after exposure to diazoacetate contained O 6 -carboxymethyl-G adducts; 96 hence it seems certain that -diazo carbonyl compounds target DNA, but determining a precise mechanism and whether this has biological relevance will require more studies.…”