Details
| Original language | English |
|---|---|
| Pages (from-to) | 459-466 |
| Number of pages | 8 |
| Journal | Zeitschrift fur Naturforschung - Section C Journal of Biosciences |
| Volume | 60 |
| Issue number | 5-6 |
| Publication status | Published - 2005 |
Abstract
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.
Keywords
- Limonene, Oxyfunctionalisation, Stereoselectivity
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- General Biochemistry,Genetics and Molecular Biology
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In: Zeitschrift fur Naturforschung - Section C Journal of Biosciences, Vol. 60, No. 5-6, 2005, p. 459-466.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Regio- and stereoselective fungal oxyfunctionalisation of limonenes
AU - Kaspera, Rüdiger
AU - Krings, Ulrich
AU - Pescheck, Michael
AU - Sell, Dieter
AU - Schrader, Jens
AU - Berger, Ralf G.
N1 - Funding information: We are grateful for the support by the Federal Minister of Education and Research (BMBF 0330062) and by Deutsche Bundesstiftung Um-welt, DBU (AZ 13053/17). The project is part of the joint initiative project “Biologisch aktive Na-turstoffe Ð Chemische Diversität“ at the University of Hannover.
PY - 2005
Y1 - 2005
N2 - 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.
AB - 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.
KW - Limonene
KW - Oxyfunctionalisation
KW - Stereoselectivity
UR - http://www.scopus.com/inward/record.url?scp=22144444214&partnerID=8YFLogxK
U2 - 10.1515/znc-2005-5-615
DO - 10.1515/znc-2005-5-615
M3 - Article
C2 - 16042348
AN - SCOPUS:22144444214
VL - 60
SP - 459
EP - 466
JO - Zeitschrift fur Naturforschung - Section C Journal of Biosciences
JF - Zeitschrift fur Naturforschung - Section C Journal of Biosciences
SN - 0939-5075
IS - 5-6
ER -