Details
| Originalsprache | Englisch |
|---|---|
| Aufsatznummer | e202401414 |
| Fachzeitschrift | CHEMCATCHEM |
| Jahrgang | 17 |
| Ausgabenummer | 1 |
| Frühes Online-Datum | 30 Sept. 2024 |
| Publikationsstatus | Veröffentlicht - 9 Jan. 2025 |
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.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
- Chemie (insg.)
- Anorganische Chemie
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in: CHEMCATCHEM, Jahrgang 17, Nr. 1, e202401414, 09.01.2025.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › 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 - 2025/1/9
Y1 - 2025/1/9
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
VL - 17
JO - CHEMCATCHEM
JF - CHEMCATCHEM
SN - 1867-3880
IS - 1
M1 - e202401414
ER -