Microbial oxidation of adamantanone by Pseudomonas putida carrying the camphor catabolic plasmid.
Intact cells of (+/-)camphor-grown Pseudomonas putida, ATCC17453(CAM), have been shown to oxidize readily the monoketone derivative of cage hydrocarbon adamantane, forming oxygenated products indicative of both biological Baeyer-Villiger and hydroxylation reactions. Formed products were identified as 4-oxahomoadamantan-5-one, 5-hydroxyadamantan-2-one and 1-hydroxy-4-oxahomoadamantan-5-one. Minor products formed as a result of secondary reactions were tentatively identified as syn- and anti-1,4-dihydroxyadamantanes and bicyclo[3.3.1]nonan-3-ol. Adamantanone initial concentrations determined whether 1-hydroxy-4-oxahomoadamantan-5-one was the sole product (below 120 mg/l) or 4-oxahomoadamantan-5-one was the principle (up to 92%) product (240-600 mg/l). Formation of 1-hydroxy-4-oxahomoadamantan-5-one appears to occur by two routes determined by the sequence of lactonization and hydroxylation.
Selifonov
S A
SA
Center for Environmental Diagnostics and Bioremediation, University of West Florida, Pensacola 32514.
D000218:Adamantane / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D001711:Biotransformation; D002164:Camphor / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010957:Plasmids; D016958:Pseudomonas putida / Q000235:genetics / Q000378:metabolism*
D002164:Camphor; D000218:Adamantane; C001862:adamantanone