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Synthesis of green note aroma compounds by biotransformation of fatty acids using yeast cells coexpressing lipoxygenase and hydroperoxide lyase.
Appl Microbiol Biotechnol. 2012 Jan; 93(1):159-68.AM

Abstract

Green notes are substances that characterize the aroma of freshly cut grass, cucumbers, green apples, and foliage. In plants, they are synthesized by conversion of linolenic or linoleic acid via the enzymes lipoxygenase (LOX) and hydroperoxide lyase (HPL) to short-chained aldehydes. Current processes for production of natural green notes rely on plant homogenates as enzyme sources but are limited by low enzyme concentration and low specificity. In an alternative approach, soybean LOX2 and watermelon HPL were overexpressed in Saccharomyces cerevisiae. After optimization of the expression constructs, a yeast strain coexpressing LOX and HPL was applied in whole cell biotransformation experiments. Whereas addition of linolenic acid to growing cultures of this strain yielded no products, we were able to identify high green note concentrations when resting cells were used. The primary biotransformation product was 3(Z)-hexenal, a small amount of which isomerized to 2(E)-hexenal. Furthermore, both aldehydes were reduced to the corresponding green note alcohols by endogenous yeast alcohol dehydrogenase to some extent. As the cosolvent ethanol was the source of reducing equivalents for green note alcohol formation, the hexenal/hexenol ratio could be influenced by the use of alternative cosolvents. Further investigations to identify the underlying mechanism of the rather low biocatalyst stability revealed a high toxicity of linolenic acid to yeast cells. The whole cell catalyst containing LOX and HPL enzyme activity described here can be a promising approach towards a highly efficient microbial green note synthesis process.

Authors+Show Affiliations

Biochemical Engineering, DECHEMA eV, Karl Winnacker-Institut, Frankfurt, Germany. buchhaupt@dechema.deNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21789493

Citation

Buchhaupt, Markus, et al. "Synthesis of Green Note Aroma Compounds By Biotransformation of Fatty Acids Using Yeast Cells Coexpressing Lipoxygenase and Hydroperoxide Lyase." Applied Microbiology and Biotechnology, vol. 93, no. 1, 2012, pp. 159-68.
Buchhaupt M, Guder JC, Etschmann MM, et al. Synthesis of green note aroma compounds by biotransformation of fatty acids using yeast cells coexpressing lipoxygenase and hydroperoxide lyase. Appl Microbiol Biotechnol. 2012;93(1):159-68.
Buchhaupt, M., Guder, J. C., Etschmann, M. M., & Schrader, J. (2012). Synthesis of green note aroma compounds by biotransformation of fatty acids using yeast cells coexpressing lipoxygenase and hydroperoxide lyase. Applied Microbiology and Biotechnology, 93(1), 159-68. https://doi.org/10.1007/s00253-011-3482-1
Buchhaupt M, et al. Synthesis of Green Note Aroma Compounds By Biotransformation of Fatty Acids Using Yeast Cells Coexpressing Lipoxygenase and Hydroperoxide Lyase. Appl Microbiol Biotechnol. 2012;93(1):159-68. PubMed PMID: 21789493.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of green note aroma compounds by biotransformation of fatty acids using yeast cells coexpressing lipoxygenase and hydroperoxide lyase. AU - Buchhaupt,Markus, AU - Guder,Jan Christopher, AU - Etschmann,Maria Magdalena Walburga, AU - Schrader,Jens, Y1 - 2011/07/26/ PY - 2011/04/13/received PY - 2011/07/13/accepted PY - 2011/07/01/revised PY - 2011/7/27/entrez PY - 2011/7/27/pubmed PY - 2012/4/20/medline SP - 159 EP - 68 JF - Applied microbiology and biotechnology JO - Appl Microbiol Biotechnol VL - 93 IS - 1 N2 - Green notes are substances that characterize the aroma of freshly cut grass, cucumbers, green apples, and foliage. In plants, they are synthesized by conversion of linolenic or linoleic acid via the enzymes lipoxygenase (LOX) and hydroperoxide lyase (HPL) to short-chained aldehydes. Current processes for production of natural green notes rely on plant homogenates as enzyme sources but are limited by low enzyme concentration and low specificity. In an alternative approach, soybean LOX2 and watermelon HPL were overexpressed in Saccharomyces cerevisiae. After optimization of the expression constructs, a yeast strain coexpressing LOX and HPL was applied in whole cell biotransformation experiments. Whereas addition of linolenic acid to growing cultures of this strain yielded no products, we were able to identify high green note concentrations when resting cells were used. The primary biotransformation product was 3(Z)-hexenal, a small amount of which isomerized to 2(E)-hexenal. Furthermore, both aldehydes were reduced to the corresponding green note alcohols by endogenous yeast alcohol dehydrogenase to some extent. As the cosolvent ethanol was the source of reducing equivalents for green note alcohol formation, the hexenal/hexenol ratio could be influenced by the use of alternative cosolvents. Further investigations to identify the underlying mechanism of the rather low biocatalyst stability revealed a high toxicity of linolenic acid to yeast cells. The whole cell catalyst containing LOX and HPL enzyme activity described here can be a promising approach towards a highly efficient microbial green note synthesis process. SN - 1432-0614 UR - https://www.unboundmedicine.com/medline/citation/21789493/Synthesis_of_green_note_aroma_compounds_by_biotransformation_of_fatty_acids_using_yeast_cells_coexpressing_lipoxygenase_and_hydroperoxide_lyase_ L2 - https://dx.doi.org/10.1007/s00253-011-3482-1 DB - PRIME DP - Unbound Medicine ER -