Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide
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...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016-08-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989016010859 |
| _version_ | 1819294612271923200 |
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| author | Melanie N. Hemgesberg Thorsten Bonck Karl-Heinz Merz Yu Sun Dieter Schrenk |
| author_facet | Melanie N. Hemgesberg Thorsten Bonck Karl-Heinz Merz Yu Sun Dieter Schrenk |
| author_sort | Melanie N. Hemgesberg |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-24T04:29:05Z |
| format | Article |
| id | doaj.art-a7bc7c9ee04b49939d6a8b952da92ee1 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T04:29:05Z |
| publishDate | 2016-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-a7bc7c9ee04b49939d6a8b952da92ee12022-12-21T17:15:29ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-08-017281179118210.1107/S2056989016010859su5309Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamideMelanie N. Hemgesberg0Thorsten Bonck1Karl-Heinz Merz2Yu Sun3Dieter Schrenk4Food Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, GermanyTheoretical Chemistry, University of Kaiserslautern, 67663 Kaiserslautern, GermanyFood Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, GermanyInorganic Chemistry, University of Kaiserslautern, 67663 Kaiserslautern, GermanyFood Chemistry and Toxicology, University of Kaiserslautern, 67663 Kaiserslautern, GermanyThe 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.http://scripts.iucr.org/cgi-bin/paper?S2056989016010859crystal structureglycidamideacrylamidemutagenicgenotoxic metabolitehydrogen bondingβ-sheet |
| spellingShingle | Melanie N. Hemgesberg Thorsten Bonck Karl-Heinz Merz Yu Sun Dieter Schrenk Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide Acta Crystallographica Section E: Crystallographic Communications crystal structure glycidamide acrylamide mutagenic genotoxic metabolite hydrogen bonding β-sheet |
| title | Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide |
| title_full | Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide |
| title_fullStr | Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide |
| title_full_unstemmed | Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide |
| title_short | Crystal structure of glycidamide: the mutagenic and genotoxic metabolite of acrylamide |
| title_sort | crystal structure of glycidamide the mutagenic and genotoxic metabolite of acrylamide |
| topic | crystal structure glycidamide acrylamide mutagenic genotoxic metabolite hydrogen bonding β-sheet |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989016010859 |
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