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Total Synthesis of Complex Biosynthetic Late-Stage Intermediates and Bioconversion by a Tailoring Enzyme from Jerangolid Biosynthesis

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 (16 November 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

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
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professur Organische Chemie - Lebensmittelchemie > Professur Organische Chemie - Lebensmittelchemie - 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 > Professur Organische Chemie - Lebensmittelchemie
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: 29 Nov 2018 09:55
URI: https://eref.uni-bayreuth.de/id/eprint/46502