Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system |
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Authors: | Marco Girhard Kazuhiro Machida Masashi Itoh Rolf D Schmid Akira Arisawa Vlada B Urlacher |
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Institution: | (1) Institute of Technical Biochemistry, Universitaet Stuttgart, Allmandring 31, Stuttgart, 70569, Germany;(2) Bioresource Laboratories, Mercian Corporation, 1808 Nakaizumi, Iwata Shizuoka, 438-0078, Japan |
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Abstract: | Background (+)-Nootkatone (4) is a high added-value compound found in grapefruit juice. Allylic oxidation of the sesquiterpene (+)-valencene (1) provides an attractive route to this sought-after flavoring. So far, chemical methods to produce (+)-nootkatone (4) from (+)-valencene (1) involve unsafe toxic compounds, whereas several biotechnological approaches applied yield large amounts of undesirable byproducts.
In the present work 125 cytochrome P450 enzymes from bacteria were tested for regioselective oxidation of (+)-valencene (1) at allylic C2-position to produce (+)-nootkatone (4) via cis- (2) or trans-nootkatol (3). The P450 activity was supported by the co-expression of putidaredoxin reductase (PdR) and putidaredoxin (Pdx) from Pseudomonas putida in Escherichia coli. |
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