• Media type: E-Article; Text
  • Title: Regio- and stereoselective fungal oxyfunctionalisation of limonenes
  • Contributor: Kaspera, Rüdiger [Author]; Krings, Ulrich [Author]; Pescheck, Michael [Author]; Sell, Dieter [Author]; Schrader, Jens [Author]; Berger, Ralf Günter [Author]
  • imprint: Berlin : De Gruyter, 2005
  • Published in: Zeitschrift für Naturforschung - Section C Journal of Biosciences 60 (2005), Nr. 5-6
  • Issue: published Version
  • Language: English
  • DOI: https://doi.org/10.15488/2473; https://doi.org/10.1515/znc-2005-5-615
  • ISSN: 0939-5075
  • Keywords: cyclohexene derivative ; Penicillium digitatum ; Limonene ; Cyclohexenes ; Stereoselectivity ; Basidiomycetes ; metabolism ; biotransformation ; Structure-Activity Relationship ; article ; Oxidation-Reduction ; Oxyfunctionalisation ; structure activity relation ; Terpenes ; Ascomycetes ; Pleurotus sapidus ; Gongronella butleri ; Fusarium proliferatum ; Penicillium citrinum ; Pleurotus ; terpene ; Ascomycota ; Basidiomycota ; oxidation reduction reaction
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  • Description: Selective transformations of limonene by asco- and basidiomycetes were investigated. On the shake flask scale, Penicillium citrinum hydrated R-(+)-limonene to α-terpineol [83% regioselectivity (rs), more than 80 mg l-1 product yield], and Gongronella butleri catalysed the terminal oxidation to yield perillyl alcohol (60% rs, 16 mg l-1). On the laboratory bioreactor scale, Penicillium digitatum produced a peak concentration of 506 mg α-terpineol l-1 in the fed-batch mode, equivalent to a theoretical yield of 67%, and no volatile by-products were found. Fusarium proliferatum transformed R-(+)-limonene enantiospecifically to cis-(+)-carveol (98.6% ee, more than 35 mg l-1 product yield) and S-(-)-limonene predominantly to trans-(-)-carveol (96.3% ee). Pleurotus sapidus selectively dehydrogenised the accumulating trans-(-)-carveol to the corresponding enantiopure R-(-)-carvone. The results show that a careful selection of strain and bioprocess parameters may improve both the yield and the optical purity of a desired product.
  • Access State: Open Access
  • Rights information: Attribution - Non Commercial - No Derivs (CC BY-NC-ND)