Selective Oxidation of 2-Methylnaphthalene to 2-Methyl-l-naphthol by Rhodococcus sp. M192

  • Biosci Biotechnol Biochem. 1996 Jan;60(5):769-72. doi: 10.1271/bbb.60.769.
H Taguchi  1 ,  S Kita  1 ,  M Kobayashi  1 ,  Y Tan  1
Affiliations
  • 1. a Department of Agricultural Chemistry, Faculty of Agriculture , Kyoto University, Sakyo-ku , Kyoto 606-01 , Japan.
PMID: 27281139 DOI: 10.1271/bbb.60.769
Abstract

About 6000 isolates of Microorganisms assimilating methylketones (C3-C6) were tested for their selective oxidation of 2-methylnaphthalene to 2-methyl-1-naphthol. Strain M192 was the highest 2-methyl-1-naphthol producer and was classified as the genus Rhodococcus. The optimal conditions for the site-specific oxidation were studied using resting Rhodococcus sp. M192. The 2-methyl-1-naphthol productivity was specifically increased using methylethylketone as a carbon source, 1-propanol as a solvent to dissolve the substrate, and ethylxanthate or diethyldithiocarbamate as an inhibitor of 2-naphthoic acid (side-product) production. In the presence of these compounds, 2-methylnaphthalene was specifically oxidized at the 1-position without the conversion to 2-naphthoic acid. The productivity of 2-methyl-1-naphthol was about 90 μM from 1 mM 2-methylnaphthalene.

Keywords
2-methyl-l-naphthol; 2-methylnaphthalene; menadione; monooxygenase; site-specific oxidation.
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