biostudies-literatureAkagi JIGovernment of Japan Ministry of Education Culture Sports Science and TechnologyJapan Society for the Promotion of Science110898https://www.ebi.ac.uk/biostudies/studies/S-EPMC12769786biostudies-literatureUnknown301(12)Acrylamide, a food contaminant, is metabolically converted to glycidamide (GA), which reacts with nucleobases in DNA. Although several GA adducts with dG, 2'-deoxyadenosine (dA), and dC are known, the mutagenic potency of each adduct remains unclear. Here, we focused on N⁶-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine (N⁶-GA-dA), which is produced by the Dimroth rearrangement of N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine. We separately prepared N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine and N⁶-GA-dA and measured their Dimroth rearrangement reaction rates. Since N⁶-GA-dA is the stable final product under physiological conditions (pH 7.0, at 37°C), we examined its presence in genomic DNA isolated from GA-treated cells. N⁶-GA-dA The Journal of biological chemistryChemical and biological characterization of glycidamide-adducted adenine in DNA.PMC12769786JPMXS0441200025Yokoi MYamaguchi RIwai SSugasawa KMiyake YAkagi JIfalseChemical and biological characterization of glycidamide-adducted adenine in DNA.Acrylamide, a food contaminant, is metabolically converted to glycidamide (GA), which reacts with nucleobases in DNA. Although several GA adducts with dG, 2'-deoxyadenosine (dA), and dC are known, the mutagenic potency of each adduct remains unclear. Here, we focused on N⁶-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine (N⁶-GA-dA), which is produced by the Dimroth rearrangement of N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine. We separately prepared N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine and N⁶-GA-dA and measured their Dimroth rearrangement reaction rates. Since N⁶-GA-dA is the stable final product under physiological conditions (pH 7.0, at 37°C), we examined its presence in genomic DNA isolated from GA-treated cells. N⁶-GA-dA 2025-01-01T00:00:00Z2025 Dec2026-06-09T05:21:20.38Z2026-06-09T03:07:59.187ZS-EPMC127697864119773410.1016/j.jbc.2025.110898