biostudies-literatureGirel SGerman Research FoundationGerman Research Foundation Priority Program4786https://www.ebi.ac.uk/biostudies/studies/S-EPMC9330447biostudies-literatureUnknown27(15)Incubation of <i>Aminobacter aminovorans</i>, <i>Paenibacillus polymyxa</i>, and <i>Arthrobacter</i> MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product <i>2</i>-acetamido-phenol, produced from 2-aminophenol, led to the recently identified <i>N</i>-(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown <i>N-</i>(2-hydroxy-5-nitrosophenyl)acetamide, and to <i>N-</i>(2-hydroxy-3-nitrophenyl)acetamide. As an alternative to the formation of phenoxazinone derived from aminophenol, dimers- and trimers-transformation products have been found. Identification of the compounds was carried out by LC/HRMS and MS/MS and, for the new structure <i>N-</i>(2-hydroxy-5-nitrosophenyl)acetamide, additionally by 1D- and 2D-NMR. Incubation of microorganisms, such as the soil bacteria <i>Molecules (Basel, Switzerland)Bioactive Nitrosylated and Nitrated <i>N</i>-(2-hydroxyphenyl)acetamides and Derived Oligomers: An Alternative Pathway to 2-Amidophenol-Derived Phytotoxic Metabolites.PMC9330447DECRyPTDo520/17SPP 2125Priority Program SPP 2125, DECRyPT, Do520/17-1)Schutz VBigler LGirel SDormann PSchulz MfalseBioactive Nitrosylated and Nitrated <i>N</i>-(2-hydroxyphenyl)acetamides and Derived Oligomers: An Alternative Pathway to 2-Amidophenol-Derived Phytotoxic Metabolites.Incubation of <i>Aminobacter aminovorans</i>, <i>Paenibacillus polymyxa</i>, and <i>Arthrobacter</i> MPI764 with the microbial 2-benzoxazolinone (BOA)-degradation-product <i>2</i>-acetamido-phenol, produced from 2-aminophenol, led to the recently identified <i>N</i>-(2-hydroxy-5-nitrophenyl) acetamide, to the hitherto unknown <i>N-</i>(2-hydroxy-5-nitrosophenyl)acetamide, and to <i>N-</i>(2-hydroxy-3-nitrophenyl)acetamide. As an alternative to the formation of phenoxazinone derived from aminophenol, dimers- and trimers-transformation products have been found. Identification of the compounds was carried out by LC/HRMS and MS/MS and, for the new structure <i>N-</i>(2-hydroxy-5-nitrosophenyl)acetamide, additionally by 1D- and 2D-NMR. Incubation of microorganisms, such as the soil bacteria <i>2022-01-01T00:00:00Z2022 Jul2026-04-08T10:48:55.028Z2024-11-09T19:32:49.31ZS-EPMC93304473589796110.3390/molecules27154786