Details
| Original language | English |
|---|---|
| Article number | e202300599 |
| Number of pages | 6 |
| Journal | CHEMBIOCHEM |
| Volume | 25 |
| Issue number | 1 |
| Early online date | 1 Nov 2023 |
| Publication status | Published - 2 Jan 2024 |
Abstract
The new farnesyl pyrophosphate (FPP) derivative with a shifted olefinic double bond from C6-C7 to C7-C8 is accepted and converted by the sesquiterpene cyclases protoilludene synthase (Omp7) as well as viridiflorene synthase (Tps32). In both cases, a so far unknown germacrene derivative was found to be formed, which we name “germacrene F”. Both cases are examples in which a modification around the central olefinic double bond in FPP leads to a change in the mode of initial cyclization (from 1→11 to 1→10). For Omp7 a rationale for this behaviour was found by carrying out molecular docking studies. Temperature-dependent NMR experiments, accompanied by NOE studies, show that germacrene F adopts a preferred mirror-symmetric conformation with both methyl groups oriented in the same directions in the cyclodecane ring.
Keywords
- biotransformation, enzyme promiscuity, germacrene, sesquiterpene cyclases, sesquiterpenes
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Medicine
- Biochemistry, Genetics and Molecular Biology(all)
- Molecular Biology
- Chemistry(all)
- Organic Chemistry
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In: CHEMBIOCHEM, Vol. 25, No. 1, e202300599, 02.01.2024.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Chemoenzymatic Synthesis of a New Germacrene Derivative Named Germacrene F
AU - Struwe, Henry
AU - Droste, Jörn
AU - Dhar, Dipendu
AU - Davari, Mehdi D.
AU - Kirschning, Andreas
N1 - Funding Information: . MDD thanks for being supported by the Leibniz Institute of Plant Biochemistry (IPB) in Halle, Germany. Open Access funding enabled and organized by Projekt DEAL
PY - 2024/1/2
Y1 - 2024/1/2
N2 - The new farnesyl pyrophosphate (FPP) derivative with a shifted olefinic double bond from C6-C7 to C7-C8 is accepted and converted by the sesquiterpene cyclases protoilludene synthase (Omp7) as well as viridiflorene synthase (Tps32). In both cases, a so far unknown germacrene derivative was found to be formed, which we name “germacrene F”. Both cases are examples in which a modification around the central olefinic double bond in FPP leads to a change in the mode of initial cyclization (from 1→11 to 1→10). For Omp7 a rationale for this behaviour was found by carrying out molecular docking studies. Temperature-dependent NMR experiments, accompanied by NOE studies, show that germacrene F adopts a preferred mirror-symmetric conformation with both methyl groups oriented in the same directions in the cyclodecane ring.
AB - The new farnesyl pyrophosphate (FPP) derivative with a shifted olefinic double bond from C6-C7 to C7-C8 is accepted and converted by the sesquiterpene cyclases protoilludene synthase (Omp7) as well as viridiflorene synthase (Tps32). In both cases, a so far unknown germacrene derivative was found to be formed, which we name “germacrene F”. Both cases are examples in which a modification around the central olefinic double bond in FPP leads to a change in the mode of initial cyclization (from 1→11 to 1→10). For Omp7 a rationale for this behaviour was found by carrying out molecular docking studies. Temperature-dependent NMR experiments, accompanied by NOE studies, show that germacrene F adopts a preferred mirror-symmetric conformation with both methyl groups oriented in the same directions in the cyclodecane ring.
KW - biotransformation
KW - enzyme promiscuity
KW - germacrene
KW - sesquiterpene cyclases
KW - sesquiterpenes
UR - http://www.scopus.com/inward/record.url?scp=85177456558&partnerID=8YFLogxK
U2 - 10.1002/cbic.202300599
DO - 10.1002/cbic.202300599
M3 - Article
C2 - 37910783
AN - SCOPUS:85177456558
VL - 25
JO - CHEMBIOCHEM
JF - CHEMBIOCHEM
SN - 1439-4227
IS - 1
M1 - e202300599
ER -