Details
| Original language | English |
|---|---|
| Pages (from-to) | 1653-1662 |
| Number of pages | 10 |
| Journal | Journal of natural products |
| Volume | 88 |
| Issue number | 7 |
| Early online date | 17 Jul 2025 |
| Publication status | Published - 25 Jul 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 subject areas
- Chemistry(all)
- Analytical Chemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Pharmacology, Toxicology and Pharmaceutics(all)
- Pharmacology
- Pharmacology, Toxicology and Pharmaceutics(all)
- Pharmaceutical Science
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Medicine(all)
- Complementary and alternative medicine
- Chemistry(all)
- Organic Chemistry
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In: Journal of natural products, Vol. 88, No. 7, 25.07.2025, p. 1653-1662.
Research output: Contribution to journal › Article › Research › 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 -