Publikation:

An Unusual Skeletal Rearrangement in the Biosynthesis of the SesquiterpeneTrichobrasilenol from Trichoderma

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2019

Autor:innen

Murai, Keiichi
Lauterbach, Lukas
Teramoto, Kazuya
Quan, Zhiyang
Barra, Lena
Yamamoto, Tsuyoshi
Nonaka, Kenichi
Shiomi, Kazuro
Dickschat, Jeroen S
et al.

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http://nbn-resolving.de/urn:nbn:de:bsz:352-2-1kzm7z1pifmpm0
DOI (zitierfähiger Link)
https://doi.org/10.1002/anie.201907964
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CC BY 4.0

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Chemie: Publikationen
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Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2019, 58(42), pp. 15046-15050. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201907964

Zusammenfassung

The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.

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540 Chemie

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ISO 690MURAI, Keiichi, Lukas LAUTERBACH, Kazuya TERAMOTO, Zhiyang QUAN, Lena BARRA, Tsuyoshi YAMAMOTO, Kenichi NONAKA, Kazuro SHIOMI, Jeroen S DICKSCHAT, 2019. An Unusual Skeletal Rearrangement in the Biosynthesis of the SesquiterpeneTrichobrasilenol from Trichoderma. In: Angewandte Chemie International Edition. Wiley-Blackwell - STM. 2019, 58(42), pp. 15046-15050. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201907964
BibTex
@article{Murai2019Unusu-57690,
  year={2019},
  doi={10.1002/anie.201907964},
  title={An Unusual Skeletal Rearrangement in the Biosynthesis of the SesquiterpeneTrichobrasilenol from Trichoderma},
  number={42},
  volume={58},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={15046--15050},
  author={Murai, Keiichi and Lauterbach, Lukas and Teramoto, Kazuya and Quan, Zhiyang and Barra, Lena and Yamamoto, Tsuyoshi and Nonaka, Kenichi and Shiomi, Kazuro and Dickschat, Jeroen S}
}
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