Regio- and stereoselective subterminal hydroxylations of n-decane by fungi in a liquid-liquid interface bioreactor (L-L IBR)

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  • Regio- and Stereoselective Subterminal Hydroxylations of <i>n</i>-Decane by Fungi in a Liquid–Liquid Interface Bioreactor (L–L IBR)
  • Regio- and stereoselective subterminal hydroxylation of n-decane by fungi in a liquid-liquid interface bioreactor (L–L IBR)
  • Regio- nd stereoselective subterminal hydroxylations of n-decane by fungi in a liquid–liquid interface bioreactor (L-L IBR)

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This article may be the first report to describe the excellent regio- and stereoselective subterminal hydroxylations of n-alkane with microorganisms. Approximately 2000 fungal strains were screened for the regioselective hydroxylation of n-decane with a solid–liquid interface bioreactor, which is a microbial transformation device on an interface between an agar plate and an organic phase (n-decane). Although Beauveria bassiana ATCC 7159, a typical fungus having a strong and versatile hydroxylating ability, mainly produced a mixture of 2-, 3-, 4-, and 5-decanone regioisomers into a n-decane layer, Monilliela sp. NAP 00702 and Rhizopus oryzae R-38-8 typically accumulated 4- and 5-decanols into the n-decane layer, respectively. Although a small amount of 4- and 5-decanones were also produced, the regioselectivity at C-4 and C-5 positions of n-decane reached 99 and 90%, respectively. Furthermore, the hydroxylation of n-decane with Monilliela sp. NAP 00702 stereoselectively proceeded to afford almost 100% ee of (−)-4-decanol.

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