TY  - JOUR
A1  - Kschowak, Max J.
A1  - Wortmann, Hannah
A1  - Dickschat, Jeroen S.
A1  - Schrader, Jens
A1  - Buchhaupt, Markus
T1  - Heterologous expression of 2-methylisoborneol / 2 methylenebornane biosynthesis genes in Escherichia coli yields novel C11-terpenes
T2  - PLoS one
N2  - The structural diversity of terpenoids is limited by the isoprene rule which states that all primary terpene synthase products derive from methyl-branched building blocks with five carbon atoms. With this study we discover a broad spectrum of novel terpenoids with eleven carbon atoms as byproducts of bacterial 2-methylisoborneol or 2-methylenebornane synthases. Both enzymes use 2-methyl-GPP as substrate, which is synthesized from GPP by the action of a methyltransferase. We used E. coli strains that heterologously produce different C11-terpene synthases together with the GPP methyltransferase and the mevalonate pathway enzymes. With this de novo approach, 35 different C11-terpenes could be produced. In addition to eleven known compounds, it was possible to detect 24 novel C11-terpenes which have not yet been described as terpene synthase products. Four of them, 3,4-dimethylcumene, 2-methylborneol and the two diastereomers of 2-methylcitronellol could be identified. Furthermore, we showed that an E. coli strain expressing the GPP-methyltransferase can produce the C16-terpene 6-methylfarnesol which indicates the condensation of 2-methyl-GPP and IPP to 6-methyl-FPP by the E. coli FPP-synthase. Our study demonstrates the broad range of unusual terpenes accessible by expression of GPP-methyltransferases and C11-terpene synthases in E. coli and provides an extended mechanism for C11-terpene synthases.
KW  - Terpenes
KW  - Mass spectra
KW  - Gas chromatography-mass spectrometry
KW  - Plasmid construction
KW  - Alcohols
KW  - Sequence analysis
KW  - Methylation
KW  - Biosynthesis
Y1  - 2018
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/46104
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-461048
SN  - 1932-6203
N1  - Copyright: © 2018 Kschowak et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
VL  - 13
IS  - (4): e0196082
SP  - 1
EP  - 15
PB  - PLoS
CY  - Lawrence, Kan.
ER  -