Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells.
Hydroxylation of adamantane using whole cells of bacteria, actinomyces, and molds was examined. The structure of the product was determined using gas chromatography (GC), nuclear magnetic resonance (NMR), and mass spectroscopy (MS). Among 470 strains tested, Streptomyces griseoplanus was highly regioselective to give 1-adamantanol (0.096 mmol) from adamantane (0.3 mmol) in a 32% molar conversion yield after 72-h cultivation in the presence of 3% (v/v) Tween 60. A P450 inhibitor such as 0.5 mM 1-aminobenzotriazole or menadione significantly inhibited the hydroxylation activity. These results suggested that a P450 oxidation system might be involved in this hydroxylation reaction.
Mitsukura
Koichi
K
Department of Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu, 501-1193, Japan. kmitsu@biomol.gifu-u.ac.jp
Kondo
Yoshinori
Y
Yoshida
Toyokazu
T
Nagasawa
Toru
T
D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D000438:Alcohols / Q000737:chemistry / Q000378:metabolism*; D002849:Chromatography, Gas; D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000494:pharmacology; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013302:Streptomyces / Q000201:enzymology / Q000378:metabolism*; D014230:Triazoles / Q000494:pharmacology; D024483:Vitamin K 3 / Q000494:pharmacology
D000438:Alcohols; D065607:Cytochrome P-450 Enzyme Inhibitors; D004791:Enzyme Inhibitors; D014230:Triazoles; C033020:1-aminobenzotriazole; C085496:2-adamantanol; D024483:Vitamin K 3; D003577:Cytochrome P-450 Enzyme System; C434445:1-adamantanol; D000218:Adamantane