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Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide.

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 ?-sheet structures enclosing R 2 (2)(8) and R 4 (2)(8) loops. The ?-sheets are linked by weaker C-H?O hydrogen bonds, forming a supra-molecular three-dimensional structure.

SUBMITTER: Hemgesberg MN

PROVIDER: S-EPMC4971867 | biostudies-other | 2016 Aug

REPOSITORIES: biostudies-other

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Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acryl-amide.

Hemgesberg Melanie N MN Bonck Thorsten T Merz Karl-Heinz KH Sun Yu Y Schrenk Dieter D

Acta crystallographica. Section E, Crystallographic communications 20160722 Pt 8

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 ...[more]

PMID: 27536408

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