Regio- and Stereoselective Fungal Oxyfunctionalisation of Limonenes
| Autor: | Ulrich Krings, Dieter Sell, Jens Schrader, Rüdiger Kaspera, Michael Pescheck, Ralf G. Berger |
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| Rok vydání: | 2005 |
| Předmět: |
Basidiomycetes
Dewey Decimal Classification::500 | Naturwissenschaften::570 | Biowissenschaften Biologie Pleurotus sapidus Gongronella butleri Fusarium proliferatum Penicillium digitatum Pleurotus General Biochemistry Genetics and Molecular Biology Structure-Activity Relationship chemistry.chemical_compound Ascomycota ddc:570 Cyclohexenes Organic chemistry Penicillium citrinum Enantiomeric excess terpene Biotransformation structure activity relation Limonene biology Terpenes Basidiomycota Perillyl alcohol article Stereoselectivity biology.organism_classification Ascomycetes Enantiopure drug chemistry Yield (chemistry) limonene metabolism oxidation reduction reaction Oxidation-Reduction cyclohexene derivative Oxyfunctionalisation |
| Zdroj: | Zeitschrift für Naturforschung-Section C Journal of Biosciences 60 (2005), Nr. 5-6 |
| ISSN: | 1865-7125 0939-5075 |
| DOI: | 10.1515/znc-2005-5-615 |
| Popis: | 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 1-1 product yield], and Gongronella butleri catalysed the terminal oxidation to yield perillyl alcohol (60% rs, 16 mg 1-1). On the laboratory bioreactor scale, Penicillium digitatum produced a peak concentration of 506 mg α-terpineol 1-1 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 1-1 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. |
| Databáze: | OpenAIRE |
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