Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 5155-5159 |
| Seitenumfang | 5 |
| Fachzeitschrift | European Journal of Organic Chemistry |
| Ausgabenummer | 27 |
| Publikationsstatus | Veröffentlicht - Sept. 2010 |
Abstract
A shunt product of chivosazole biosynthesis was isolated from the fermentation broth of Sorangium cellulosum, strain So ce 12. Its structure was elucidated by NMR spectroscopy and exhibits six chiral centers, a triene, and a labile β-hydroxy ketone. The synthesis of chivotriene confirms the structure and in particular the proposed configuration at C22, which was originally deduced for chivosazole from the combination of its genetic and spectroscopic analyses. Remarkably, chivotriene exhibits biological activity usually not observed for segments of complex natural products. However, this activity is not connected to interference with the actin cytoskeleton, the intrinsic target of the chivosazoles.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: European Journal of Organic Chemistry, Nr. 27, 09.2010, S. 5155-5159.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Isolation and synthesis of chivotriene, a chivosazole shunt product from Sorangium cellulosum
AU - Brodmann, Tobias
AU - Janssen, Dominic
AU - Sasse, Florenz
AU - Irschik, Herbert
AU - Jansen, Rolf
AU - Müller, Rolf
AU - Kalesse, Markus
PY - 2010/9
Y1 - 2010/9
N2 - A shunt product of chivosazole biosynthesis was isolated from the fermentation broth of Sorangium cellulosum, strain So ce 12. Its structure was elucidated by NMR spectroscopy and exhibits six chiral centers, a triene, and a labile β-hydroxy ketone. The synthesis of chivotriene confirms the structure and in particular the proposed configuration at C22, which was originally deduced for chivosazole from the combination of its genetic and spectroscopic analyses. Remarkably, chivotriene exhibits biological activity usually not observed for segments of complex natural products. However, this activity is not connected to interference with the actin cytoskeleton, the intrinsic target of the chivosazoles.
AB - A shunt product of chivosazole biosynthesis was isolated from the fermentation broth of Sorangium cellulosum, strain So ce 12. Its structure was elucidated by NMR spectroscopy and exhibits six chiral centers, a triene, and a labile β-hydroxy ketone. The synthesis of chivotriene confirms the structure and in particular the proposed configuration at C22, which was originally deduced for chivosazole from the combination of its genetic and spectroscopic analyses. Remarkably, chivotriene exhibits biological activity usually not observed for segments of complex natural products. However, this activity is not connected to interference with the actin cytoskeleton, the intrinsic target of the chivosazoles.
KW - Biosynthesis
KW - Chirality
KW - Natural products
KW - Structure elucidation
UR - http://www.scopus.com/inward/record.url?scp=77956473063&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201000781
DO - 10.1002/ejoc.201000781
M3 - Article
AN - SCOPUS:77956473063
SP - 5155
EP - 5159
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 27
ER -