Identification of metabolites produced from N-phenylpiperazine by Mycobacterium spp.
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.
Adjei
M D
MD
Division of Microbiology, National Center for Toxicological Research, US Food and Drug Administration, 3900 NCTR Road, Jefferson, AR 72079, USA.
Deck
J
J
Heinze
T M
TM
Freeman
J P
JP
Williams
A J
AJ
Sutherland
J B
JB
D009682:Magnetic Resonance Spectroscopy; D009161:Mycobacterium / Q000378:metabolism*; D010879:Piperazines / Q000378:metabolism*; D021241:Spectrometry, Mass, Electrospray Ionization
D010879:Piperazines; C031503:phenylpiperazine