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http://dx.doi.org/10.18419/opus-13582
Autor(en): | Aberle, Benjamin Kowalczyk, Daniel Massini, Simon Egler‐Kemmerer, Alexander‐N. Gergel, Sebastian Hammer, Stephan C. Hauer, Bernhard |
Titel: | Methylation of unactivated alkenes with engineered methyltransferases to generate non‐natural terpenoids |
Erscheinungsdatum: | 2023 |
Dokumentart: | Zeitschriftenartikel |
Seiten: | 7 |
Erschienen in: | Angewandte Chemie international edition 62 (2023), No. e202301601 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-136017 http://elib.uni-stuttgart.de/handle/11682/13601 http://dx.doi.org/10.18419/opus-13582 |
ISSN: | 1433-7851 1521-3773 |
Zusammenfassung: | Terpenoids are built from isoprene building blocks and have numerous biological functions. Selective late-stage modification of their carbon scaffold has the potential to optimize or transform their biological activities. However, the synthesis of terpenoids with a non-natural carbon scaffold is often a challenging endeavor because of the complexity of these molecules. Herein we report the identification and engineering of (S)-adenosyl-l-methionine-dependent sterol methyltransferases for selective C-methylation of linear terpenoids. The engineered enzyme catalyzes selective methylation of unactivated alkenes in mono-, sesqui- and diterpenoids to produce C11, C16 and C21 derivatives. Preparative conversion and product isolation reveals that this biocatalyst performs C-C bond formation with high chemo- and regioselectivity. The alkene methylation most likely proceeds via a carbocation intermediate and regioselective deprotonation. This method opens new avenues for modifying the carbon scaffold of alkenes in general and terpenoids in particular. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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ANIE_ANIE202301601.pdf | 3,41 MB | Adobe PDF | Öffnen/Anzeigen |
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