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http://dx.doi.org/10.18419/opus-13582
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DC Element | Wert | Sprache |
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dc.contributor.author | Aberle, Benjamin | - |
dc.contributor.author | Kowalczyk, Daniel | - |
dc.contributor.author | Massini, Simon | - |
dc.contributor.author | Egler‐Kemmerer, Alexander‐N. | - |
dc.contributor.author | Gergel, Sebastian | - |
dc.contributor.author | Hammer, Stephan C. | - |
dc.contributor.author | Hauer, Bernhard | - |
dc.date.accessioned | 2023-10-12T07:45:16Z | - |
dc.date.available | 2023-10-12T07:45:16Z | - |
dc.date.issued | 2023 | de |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.issn | 1521-3773 | - |
dc.identifier.other | 1868998266 | - |
dc.identifier.uri | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-136017 | de |
dc.identifier.uri | http://elib.uni-stuttgart.de/handle/11682/13601 | - |
dc.identifier.uri | http://dx.doi.org/10.18419/opus-13582 | - |
dc.description.abstract | 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. | en |
dc.description.sponsorship | Bundesministerium für Bildung und Forschung | de |
dc.description.sponsorship | Projekt DEAL | de |
dc.language.iso | en | de |
dc.relation.uri | doi:10.1002/anie.202301601 | de |
dc.rights | info:eu-repo/semantics/openAccess | de |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | de |
dc.subject.ddc | 540 | de |
dc.title | Methylation of unactivated alkenes with engineered methyltransferases to generate non‐natural terpenoids | en |
dc.type | article | de |
dc.date.updated | 2023-07-11T22:14:33Z | - |
ubs.fakultaet | Chemie | de |
ubs.fakultaet | Fakultätsübergreifend / Sonstige Einrichtung | de |
ubs.institut | Institut für Biochemie und Technische Biochemie | de |
ubs.institut | Fakultätsübergreifend / Sonstige Einrichtung | de |
ubs.publikation.seiten | 7 | de |
ubs.publikation.source | Angewandte Chemie international edition 62 (2023), No. e202301601 | de |
ubs.publikation.typ | Zeitschriftenartikel | de |
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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