Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 525-536 |
| Seitenumfang | 12 |
| Fachzeitschrift | Journal of the American Chemical Society |
| Jahrgang | 148 |
| Ausgabenummer | 1 |
| Frühes Online-Datum | 22 Dez. 2025 |
| Publikationsstatus | Veröffentlicht - 14 Jan. 2026 |
Abstract
Sesquiterpene synthases (STSs) enable cationic cascade reactions with farnesyl pyrophosphate (FPP) resulting in an immense variety of oligocyclic sesquiterpenes. Their substrate promiscuity allows access to new sesquiterpene carbon skeletons. We explored the ability of eight STSs to process three distinct synthetic FPP derivatives modified at the central isoprenyl unit. These include the incorporation of a keto group at C7 (“keto”-FPP), the relocation of the olefinic double bond into the methyl group (“iso”-FPP), and the shift of the double bond toward the aliphatic terminus of the FPP backbone and loss of the methyl group at C7 (“nor-iso” FPP). We report the enzymatic production of 18 new terpenoids, including a large variety of new oxaterpenoids. One of these is known as a late stage intermediate in the total synthesis of the sex pheromone periplanone B, which is secreted by females of the American cockroach Periplaneta americana to attract mates. Thus, a formal chemoenzymatic synthesis of this pheromone is disclosed.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Chemie (insg.)
- Allgemeine Chemie
- Chemische Verfahrenstechnik (insg.)
- Kolloid- und Oberflächenchemie
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in: Journal of the American Chemical Society, Jahrgang 148, Nr. 1, 14.01.2026, S. 525-536.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Chemoenzymatic Synthesis of Structurally Diverse Terpenoids from Farnesyl Pyrophosphates Modified at the Central Alkene Unit
AU - Struwe, Henry
AU - Slotman, Christopher
AU - Höft, Laurent
AU - Dräger, Gerald
AU - Droste, Jörn
AU - Fohrer, Jörg
AU - Hausmann, Katharina
AU - Beutel, Sascha
AU - Kolling, Dominik
AU - Köhnke, Jesko
AU - Kirschning, Andreas
N1 - Publisher Copyright: © 2025 The Authors. Published by American Chemical Society
PY - 2026/1/14
Y1 - 2026/1/14
N2 - Sesquiterpene synthases (STSs) enable cationic cascade reactions with farnesyl pyrophosphate (FPP) resulting in an immense variety of oligocyclic sesquiterpenes. Their substrate promiscuity allows access to new sesquiterpene carbon skeletons. We explored the ability of eight STSs to process three distinct synthetic FPP derivatives modified at the central isoprenyl unit. These include the incorporation of a keto group at C7 (“keto”-FPP), the relocation of the olefinic double bond into the methyl group (“iso”-FPP), and the shift of the double bond toward the aliphatic terminus of the FPP backbone and loss of the methyl group at C7 (“nor-iso” FPP). We report the enzymatic production of 18 new terpenoids, including a large variety of new oxaterpenoids. One of these is known as a late stage intermediate in the total synthesis of the sex pheromone periplanone B, which is secreted by females of the American cockroach Periplaneta americana to attract mates. Thus, a formal chemoenzymatic synthesis of this pheromone is disclosed.
AB - Sesquiterpene synthases (STSs) enable cationic cascade reactions with farnesyl pyrophosphate (FPP) resulting in an immense variety of oligocyclic sesquiterpenes. Their substrate promiscuity allows access to new sesquiterpene carbon skeletons. We explored the ability of eight STSs to process three distinct synthetic FPP derivatives modified at the central isoprenyl unit. These include the incorporation of a keto group at C7 (“keto”-FPP), the relocation of the olefinic double bond into the methyl group (“iso”-FPP), and the shift of the double bond toward the aliphatic terminus of the FPP backbone and loss of the methyl group at C7 (“nor-iso” FPP). We report the enzymatic production of 18 new terpenoids, including a large variety of new oxaterpenoids. One of these is known as a late stage intermediate in the total synthesis of the sex pheromone periplanone B, which is secreted by females of the American cockroach Periplaneta americana to attract mates. Thus, a formal chemoenzymatic synthesis of this pheromone is disclosed.
UR - http://www.scopus.com/inward/record.url?scp=105027583362&partnerID=8YFLogxK
U2 - 10.1021/jacs.5c14636
DO - 10.1021/jacs.5c14636
M3 - Article
C2 - 41429570
AN - SCOPUS:105027583362
VL - 148
SP - 525
EP - 536
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 1
ER -