Details
| Original language | English |
|---|---|
| Pages (from-to) | 8575-8579 |
| Number of pages | 5 |
| Journal | Organic letters |
| Volume | 25 |
| Issue number | 48 |
| Early online date | 27 Nov 2023 |
| Publication status | Published - 8 Dec 2023 |
Abstract
New sesquiterpene backbones are accessible after incubation of caryolan-synthase (GcoA) and presilphiperfolan-8-β-ol synthase (BcBOT2) with a non-natural farnesyldiphosphate in which the central olefinic double bond is isomerized toward the methyl group. Two newly formed sesquiterpenoids are reported, a constitutional isomer of caryolan-1-ol (3), which we name iso-caryolan-1-ol (17), and the first terpenoid based on the isoclovane ring skeleton generated enzymatically thus far.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 25, No. 48, 08.12.2023, p. 8575-8579.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Sesquiterpene Backbones Generated by Sesquiterpene Cyclases
T2 - Formation of iso-Caryolan-1-ol and an Isoclovane
AU - Struwe, Henry
AU - Schrödter, Finn
AU - Spinck, Hanke
AU - Kirschning, Andreas
N1 - Funding information: We thank Dr. Jörn Droste (Leibniz University Hannover) for expert support in all issues concerning NMR spectroscopic analysis.
PY - 2023/12/8
Y1 - 2023/12/8
N2 - New sesquiterpene backbones are accessible after incubation of caryolan-synthase (GcoA) and presilphiperfolan-8-β-ol synthase (BcBOT2) with a non-natural farnesyldiphosphate in which the central olefinic double bond is isomerized toward the methyl group. Two newly formed sesquiterpenoids are reported, a constitutional isomer of caryolan-1-ol (3), which we name iso-caryolan-1-ol (17), and the first terpenoid based on the isoclovane ring skeleton generated enzymatically thus far.
AB - New sesquiterpene backbones are accessible after incubation of caryolan-synthase (GcoA) and presilphiperfolan-8-β-ol synthase (BcBOT2) with a non-natural farnesyldiphosphate in which the central olefinic double bond is isomerized toward the methyl group. Two newly formed sesquiterpenoids are reported, a constitutional isomer of caryolan-1-ol (3), which we name iso-caryolan-1-ol (17), and the first terpenoid based on the isoclovane ring skeleton generated enzymatically thus far.
UR - http://www.scopus.com/inward/record.url?scp=85179612914&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.3c03383
DO - 10.1021/acs.orglett.3c03383
M3 - Article
C2 - 38011332
AN - SCOPUS:85179612914
VL - 25
SP - 8575
EP - 8579
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 48
ER -