Details
| Original language | English |
|---|---|
| Journal | CHEMCATCHEM |
| Early online date | 30 Sept 2024 |
| Publication status | E-pub ahead of print - 30 Sept 2024 |
Abstract
An unnatural tricyclic oxaterpenoid, obtained by treatment of the sesquiterpene synthase presilphiperfolan-8β-ol synthase (BcBOT2) with an unnatural farnesyl pyrophosphate ether derivative, itself obtained by chemical synthesis, was converted in oxidation studies as part of a broad screening program by selected unspecific peroxygenases (UPOs). Product analysis revealed that Agrocybe aegerita UPO, its mutant PaDa-I, and two commercial ones, UPO54 and UPO49, provided new oxidation products with sufficient efficiency for subsequent upscaling that allowed product isolation and structure elucidation. As such new terpene-based oxiranes and hemiacetals were formed by UPO-mediated epoxidations and CH-activation. The structure elucidation was further supported by comparison with products generated by chemical oxidation.
Keywords
- Biocatalysis, CH-activation, Terpene synthases, Terpenoids, Unspecific peroxygenases
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: CHEMCATCHEM, 30.09.2024.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Expanding the “Terpenome”
T2 - Applications of Unspecific Peroxygenases (UPOs) in Oxidations of Unnatural Terpenoids
AU - Struwe, Henry
AU - Grimm, Christopher
AU - Dräger, Gerald
AU - Beutel, Sascha
AU - Alcalde, Miguel
AU - Kirschning, Andreas
AU - Kara, Selin
N1 - Publisher Copyright: © 2024 The Author(s). ChemCatChem published by Wiley-VCH GmbH.
PY - 2024/9/30
Y1 - 2024/9/30
N2 - An unnatural tricyclic oxaterpenoid, obtained by treatment of the sesquiterpene synthase presilphiperfolan-8β-ol synthase (BcBOT2) with an unnatural farnesyl pyrophosphate ether derivative, itself obtained by chemical synthesis, was converted in oxidation studies as part of a broad screening program by selected unspecific peroxygenases (UPOs). Product analysis revealed that Agrocybe aegerita UPO, its mutant PaDa-I, and two commercial ones, UPO54 and UPO49, provided new oxidation products with sufficient efficiency for subsequent upscaling that allowed product isolation and structure elucidation. As such new terpene-based oxiranes and hemiacetals were formed by UPO-mediated epoxidations and CH-activation. The structure elucidation was further supported by comparison with products generated by chemical oxidation.
AB - An unnatural tricyclic oxaterpenoid, obtained by treatment of the sesquiterpene synthase presilphiperfolan-8β-ol synthase (BcBOT2) with an unnatural farnesyl pyrophosphate ether derivative, itself obtained by chemical synthesis, was converted in oxidation studies as part of a broad screening program by selected unspecific peroxygenases (UPOs). Product analysis revealed that Agrocybe aegerita UPO, its mutant PaDa-I, and two commercial ones, UPO54 and UPO49, provided new oxidation products with sufficient efficiency for subsequent upscaling that allowed product isolation and structure elucidation. As such new terpene-based oxiranes and hemiacetals were formed by UPO-mediated epoxidations and CH-activation. The structure elucidation was further supported by comparison with products generated by chemical oxidation.
KW - Biocatalysis
KW - CH-activation
KW - Terpene synthases
KW - Terpenoids
KW - Unspecific peroxygenases
UR - http://www.scopus.com/inward/record.url?scp=85205899888&partnerID=8YFLogxK
U2 - 10.1002/cctc.202401414
DO - 10.1002/cctc.202401414
M3 - Article
AN - SCOPUS:85205899888
JO - CHEMCATCHEM
JF - CHEMCATCHEM
SN - 1867-3880
ER -