Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 1653-1662 |
| Seitenumfang | 10 |
| Fachzeitschrift | Journal of natural products |
| Jahrgang | 88 |
| Ausgabenummer | 7 |
| Frühes Online-Datum | 17 Juli 2025 |
| Publikationsstatus | Veröffentlicht - 25 Juli 2025 |
Abstract
The synthesis of 8-thio-farnesylpyrophosphate is reported, which was subjected to biotransformations with different sesquiterpene synthases. The 9-thio-analogues of δ-cadinene and δ-cadinol were formed by the sesquiterpene synthases Cop4 and Omp7. In contrast, the fungal sesquiterpene synthase BcBOT2 yielded a diquinane terpenoid that contains a keto and thiol group. The formation of the two former "sulfo"-terpenoids can be rationalized by following the route proposed for δ-cadinene and δ-cadinol. The latter can be regarded by the result of a late-stage hydrolysis product during the analogous pathway to presilphiperfolan-8β-ol, the natural product of BcBOT2. The olfactoric analysis of the three "sulfo"-sesuiterpenoids revealed a stale odor for the cadinene derivatives, whereas the ketothiol diquinane exhibits a spicy aroma with a subtle chili note.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Analytische Chemie
- Biochemie, Genetik und Molekularbiologie (insg.)
- Molekularmedizin
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Pharmakologie
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Pharmazeutische Wissenschaften
- Pharmakologie, Toxikologie und Pharmazie (insg.)
- Wirkstoffforschung
- Medizin (insg.)
- Ergänzende und alternative Medizin
- Chemie (insg.)
- Organische Chemie
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in: Journal of natural products, Jahrgang 88, Nr. 7, 25.07.2025, S. 1653-1662.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Chemoenzymatic Generation of Thio-analogues of δ-Cadinene, δ-Cadinol, and a Thio-diquinane Using 8-Thio-farnesylpyrophosphate
AU - Jäger, Birk
AU - Budde, Jan Luca
AU - Birke, Norman
AU - Hauke, Maximilian
AU - Kirschning, Andreas
PY - 2025/7/25
Y1 - 2025/7/25
N2 - The synthesis of 8-thio-farnesylpyrophosphate is reported, which was subjected to biotransformations with different sesquiterpene synthases. The 9-thio-analogues of δ-cadinene and δ-cadinol were formed by the sesquiterpene synthases Cop4 and Omp7. In contrast, the fungal sesquiterpene synthase BcBOT2 yielded a diquinane terpenoid that contains a keto and thiol group. The formation of the two former "sulfo"-terpenoids can be rationalized by following the route proposed for δ-cadinene and δ-cadinol. The latter can be regarded by the result of a late-stage hydrolysis product during the analogous pathway to presilphiperfolan-8β-ol, the natural product of BcBOT2. The olfactoric analysis of the three "sulfo"-sesuiterpenoids revealed a stale odor for the cadinene derivatives, whereas the ketothiol diquinane exhibits a spicy aroma with a subtle chili note.
AB - The synthesis of 8-thio-farnesylpyrophosphate is reported, which was subjected to biotransformations with different sesquiterpene synthases. The 9-thio-analogues of δ-cadinene and δ-cadinol were formed by the sesquiterpene synthases Cop4 and Omp7. In contrast, the fungal sesquiterpene synthase BcBOT2 yielded a diquinane terpenoid that contains a keto and thiol group. The formation of the two former "sulfo"-terpenoids can be rationalized by following the route proposed for δ-cadinene and δ-cadinol. The latter can be regarded by the result of a late-stage hydrolysis product during the analogous pathway to presilphiperfolan-8β-ol, the natural product of BcBOT2. The olfactoric analysis of the three "sulfo"-sesuiterpenoids revealed a stale odor for the cadinene derivatives, whereas the ketothiol diquinane exhibits a spicy aroma with a subtle chili note.
UR - http://www.scopus.com/inward/record.url?scp=105012419550&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.5c00409
DO - 10.1021/acs.jnatprod.5c00409
M3 - Article
C2 - 40673503
AN - SCOPUS:105012419550
VL - 88
SP - 1653
EP - 1662
JO - Journal of natural products
JF - Journal of natural products
SN - 0163-3864
IS - 7
ER -