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Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture
Laboratory of Plant Biotechnologies, Joint Laboratory of Institute of Experimental Botany, Academy of Sciences of the Czech Republic, v.v.i., and Research Institute of Crop Production, v.v.i., Rozvojova 263, 165 02 Prague 6, Czech Republic
Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Albertov 6, 128 43 Prague 2, Czech Republic
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nam. 2, 166 10 Prague 6, Czech Republic
* Authors to whom correspondence should be addressed.
Received: 4 November 2011; in revised form: 5 December 2011 / Accepted: 12 December 2011 / Published: 19 December 2011
(This article belongs to the Special Issue Terpenoids
Abstract: Biotransformation of (1S)-2-carene and (1S)-3-carene by Picea abies suspension culture led to the formation of oxygenated products. (1S)-2-Carene was transformed slowly and the final product was identified as (1S)-2-caren-4-one. On the other hand, the transformation of (1S)-3-carene was rapid and finally led to the formation of (1S)-3-caren-5-one and (1S)-2-caren-4-one as equally abundant major products. The time-course of the reaction indicates that some products abundant at the beginning of the reaction (e.g. (1S,3S,4R)-3,4-epoxycarane and (1R)-p-mentha-1(7),2-dien-8-ol) were consumed by a subsequent transformations. Thus, a precise selection of the biotransformation time may be used for a production of specific compounds.
Keywords: biotransformation; carene; oxidation; Picea abies
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Dvorakova, M.; Valterova, I.; Saman, D.; Vanek, T. Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture. Molecules 2011, 16, 10541-10555.
Dvorakova M, Valterova I, Saman D, Vanek T. Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture. Molecules. 2011; 16(12):10541-10555.
Dvorakova, Marcela; Valterova, Irena; Saman, David; Vanek, Tomas. 2011. "Biotransformation of (1S)-2-Carene and (1S)-3-Carene by Picea abies Suspension Culture." Molecules 16, no. 12: 10541-10555.