White Rot Fungi Produce Novel Tire Wear Compound Metabolites and Reveal Underappreciated Amino Acid Conjugation Pathways

, removed 81.9% and 69.6% of acetanilide and HMMM, respectively, with no significant sorption to biomass. The bicyclic amine 1,3-diphenylguanidine was not removed. Additionally, we identified novel TWC metabolites using semi-untargeted metabolomics via high-resolution mass spectrometry. Key metabolites include multiple isomers of HMMM biotransformation products, melamine as a possible "dead-end" product of HMMM (verified with an authentic standard), and a glutamine-conjugated product of acetanilide. These metabolites have implications for environmental toxicity and treatment. Our discovery of the first fungal glutamine-conjugated product highlights the need to investigate amino acid conjugation as an important pathway in biotransformation of contaminants, with implications in other fields including natural products discovery.