title: Identification of metabolites produced from N-phenylpiperazine by Mycobacterium spp.
abstract: Mycobacterium sp. 7E1B1W and seven other mycobacterial strains known to degrade hydrocarbons were investigated to determine their ability to metabolize the piperazine ring, a substructure found in many drugs. Cultures were grown at 30 degrees C in tryptic soy broth and dosed with 3.1 mM N-phenylpiperazine hydrochloride; samples were removed at intervals and extracted with ethyl acetate. Two metabolites were purified from each of the extracts by high-performance liquid chromatography; they were identified by mass spectrometry and (1)H nuclear magnetic resonance spectroscopy as N-(2-anilinoethyl)acetamide and N-acetyl-N'-phenylpiperazine. The results show that mycobacteria have the ability to acetylate piperazine rings and cleave carbon-nitrogen bonds.
authors.affiliation: Division of Microbiology, National Center for Toxicological Research, US Food and Drug Administration, 3900 NCTR Road, Jefferson, AR 72079, USA.
authors.forename: M D
authors.initials: MD
authors.lastname: Adjei
authors.forename: J
authors.initials: J
authors.lastname: Deck
authors.forename: T M
authors.initials: TM
authors.lastname: Heinze
authors.forename: J P
authors.initials: JP
authors.lastname: Freeman
authors.forename: A J
authors.initials: AJ
authors.lastname: Williams
authors.forename: J B
authors.initials: JB
authors.lastname: Sutherland
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000378:metabolism*; D010879:Piperazines / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D010879:Piperazines; C031503:phenylpiperazine