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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2016: 0.631

SCImago Journal Rank (SJR) 2016: 0.237
Source Normalized Impact per Paper (SNIP) 2016: 0.332

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1865-7117
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Volume 67, Issue 10 (Oct 2012)

Issues

Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide

Lars O. Wiemann
  • Corresponding author
  • Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik IGB, Projektgruppe BioCat, Schulgasse 11a, 94315 Straubing, Germany
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/ Christina Faltl
  • Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik IGB, Projektgruppe BioCat, Schulgasse 11a, 94315 Straubing, Germany
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Volker Sieber
  • Fraunhofer Institut für Grenzflächen- und Bioverfahrenstechnik IGB, Projektgruppe BioCat, Schulgasse 11a, 94315 Straubing, Germany
  • Technische Universität München, Lehrstuhl Chemie biogener Rohstoffe, Schulgasse 16, 94315 Straubing, Germany
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Published Online: 2014-06-02 | DOI: https://doi.org/10.5560/znb.2012-0167

Limonene is an industrially interesting monoterpene that accumulates in bulk quantities as byproduct of the fruit juice industry. The corresponding epoxides are versatile synthetic intermediates and additives for the chemical industry. Due to a number of disadvantages of classical chemical epoxidation including serious safety issues and unwanted side-reactions, we here used a mild lipasecatalyzed chemo-enzymatic epoxidation system, with either free or different immobilized forms of Candida antarctica lipase B. Full limonene conversion (> 98%) was easily achieved at 40°C within less than 24 h. The enzymatic activities in the formation of limonene monoxide significantly varied from either 1 - 3:4 U/mgbiocatalyst at r. t. or from 1.7 - 4:9 U/mgbiocatalyst at 40°C. For the first time we showed that it is possible to generate high amounts of limonene dioxide (~ 30% with CalB on carrier 350 at 40°C) using this mild lipase-mediated epoxidation method. Enzyme activities and limonene dioxide yields strongly depend on the nature of the selected enzyme carrier, the immobilization method and the reaction temperature.

Graphical Abstract

Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide

Lipase-mediated Epoxidation of the Cyclic Monoterpene Limonene to Limonene Oxide and Limonene Dioxide

Keywords : Terpene; Biocatalysis; Chemo-enzymatic Epoxidation; Enzyme Immobilization; Renewable Resources

About the article

Received: 2012-06-18

Published Online: 2014-06-02

Published in Print: 2012-10-01


Citation Information: Zeitschrift für Naturforschung B, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.5560/znb.2012-0167.

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© 1946 – 2014: Verlag der Zeitschrift für Naturforschung. This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License. BY-NC-ND 3.0

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