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Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells

Abstract

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.

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Acknowledgements

We are grateful to Life Science Research Center of Gifu University for NMR and mass spectroscopy.

Author information

Correspondence to Koichi Mitsukura.

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Mitsukura, K., Kondo, Y., Yoshida, T. et al. Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells. Appl Microbiol Biotechnol 71, 502–504 (2006). https://doi.org/10.1007/s00253-005-0167-7

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Keywords

  • Nuclear Magnetic Resonance
  • P450 Inhibitor
  • Menadione
  • Adamantane
  • Hydroxylation Activity