Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide

Abstract

The title compound, glycidamide (systematic name: oxirane-2-carboxamide), C3H5NO2, is the mutagenic and genotoxic metabolite of acrylamide, a food contaminant and industrial chemical that has been classified as being probably carcinogenic to humans. Synthesized via the reaction of acrylonitrile and hydrogen peroxide, it crystallizes with both enantiomers occurring as two crystallographically independent molecules (A and B) in the asymmetric unit. They have similar conformations with an r.m.s. deviation of 0.0809 Å for molecule B inverted on molecule A. In the crystal, molecules are linked by N—H...O hydrogen bonds, which lead to the formation of β-sheet structures enclosing R22(8) and R42(8) loops. The β-sheets are linked by weaker C—H...O hydrogen bonds, forming a supramolecular three-dimensional structure.

Keywords

• crystal structure
• glycidamide
• acrylamide
• mutagenic
• genotoxic metabolite
• hydrogen bonding
• β-sheet