{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["72(Pt 8)"],"submitter":["Hemgesberg MN"],"pubmed_abstract":["The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C3H5NO2, is the mutagenic and genotoxic metabolite of acryl-amide, a food contaminant and industrial chemical that has been classified as being probably carcinogenic to humans. Synthesized via the reaction of acrylo-nitrile and hydrogen peroxide, it crystallizes with both enanti-omers occurring as two crystallographically independent mol-ecules (A and B) in the asymmetric unit. They have similar conformations with an r.m.s. deviation of 0.0809 Å for mol-ecule B inverted on mol-ecule A. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, which lead to the formation of β-sheet structures enclosing R 2 (2)(8) and R 4 (2)(8) loops. The β-sheets are linked by weaker C-H⋯O hydrogen bonds, forming a supra-molecul"],"journal":["Acta crystallographica. Section E, Crystallographic communications"],"pagination":["1179-82"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4971867"],"repository":["biostudies-literature"],"pubmed_title":["Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide."],"pmcid":["PMC4971867"],"pubmed_authors":["Hemgesberg MN","Merz KH","Schrenk D","Bonck T","Sun Y"],"additional_accession":[]},"is_claimable":false,"name":"Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide.","description":"The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C3H5NO2, is the mutagenic and genotoxic metabolite of acryl-amide, a food contaminant and industrial chemical that has been classified as being probably carcinogenic to humans. Synthesized via the reaction of acrylo-nitrile and hydrogen peroxide, it crystallizes with both enanti-omers occurring as two crystallographically independent mol-ecules (A and B) in the asymmetric unit. They have similar conformations with an r.m.s. deviation of 0.0809 Å for mol-ecule B inverted on mol-ecule A. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, which lead to the formation of β-sheet structures enclosing R 2 (2)(8) and R 4 (2)(8) loops. The β-sheets are linked by weaker C-H⋯O hydrogen bonds, forming a supra-molecul","dates":{"release":"2016-01-01T00:00:00Z","publication":"2016 Aug","modification":"2025-04-29T10:52:16.697Z","creation":"2019-03-27T02:19:48Z"},"accession":"S-EPMC4971867","cross_references":{"pubmed":["27536408"],"doi":["10.1107/S2056989016010859"]}}