Title data
Lindner, Frederick ; Friedrich, Steffen ; Hahn, Frank:
Total Synthesis of Complex Biosynthetic Late-Stage Intermediates and Bioconversion by a Tailoring Enzyme from Jerangolid Biosynthesis.
In: The Journal of Organic Chemistry.
Vol. 83
(2018)
Issue 22
.
- pp. 14091-14101.
ISSN 1520-6904
DOI: https://doi.org/10.1021/acs.joc.8b02047
Project information
Project financing: |
7. Forschungsrahmenprogramm für Forschung, technologische Entwicklung und Demonstration der Europäischen Union Deutsche Forschungsgemeinschaft |
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Abstract in another language
A highly convergent access to the late-stage biosynthetic intermediates projerangolid and jerangolid E is presented, and its utility is demonstrated by the synthesis of novel non-natural jerangolid derivatives. The key steps are fragment couplings by Julia−Kocienski olefination and olefin cross metathesis, as well as a stereoselective tetrahydropyran formation by intramolecular oxa-Michael addition. Bioconversion experiments with the tailoring O-methyltransferase JerF confirmed its proposed biosynthetic role and revealed relaxed substrate specificity of this enzyme as well as tolerance to organic cosolvents.
Further data
Item Type: | Article in a journal |
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Refereed: | Yes |
Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry - Food Chemistry > Professor Organic Chemistry - Food Chemistry - Univ.-Prof. Dr. Frank Hahn Profile Fields > Advanced Fields > Molecular Biosciences Profile Fields > Emerging Fields > Food and Health Sciences Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Organic Chemistry - Food Chemistry Profile Fields Profile Fields > Advanced Fields Profile Fields > Emerging Fields |
Result of work at the UBT: | Yes |
DDC Subjects: | 500 Science > 540 Chemistry |
Date Deposited: | 29 Nov 2018 09:55 |
Last Modified: | 21 Jan 2022 11:34 |
URI: | https://eref.uni-bayreuth.de/id/eprint/46502 |