Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids

Aberle B, Kowalczyk D, Massini S, Egler-Kemmerer A-N, Gergel S, Hammer S, Hauer B (2023)
Angewandte Chemie International Edition 62(26): e202301601.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Aberle, Benjamin; Kowalczyk, Daniel; Massini, Simon; Egler-Kemmerer, Alexander-Nicholas; Gergel, SebastianUniBi; Hammer, StephanUniBi ; Hauer, Bernhard
Abstract / Bemerkung
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 meth- yltransferases 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 meth- ylation most likely proceeds via a carbocation intermedi- ate and regioselective deprotonation. This method opens new avenues for modifying the carbon scaffold of alkenes in general and terpenoids in particular
Erscheinungsjahr
2023
Zeitschriftentitel
Angewandte Chemie International Edition
Band
62
Ausgabe
26
Art.-Nr.
e202301601
ISSN
1433-7851
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2977971

Zitieren

Aberle B, Kowalczyk D, Massini S, et al. Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids. Angewandte Chemie International Edition. 2023;62(26): e202301601.
Aberle, B., Kowalczyk, D., Massini, S., Egler-Kemmerer, A. - N., Gergel, S., Hammer, S., & Hauer, B. (2023). Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids. Angewandte Chemie International Edition, 62(26), e202301601. https://doi.org/10.1002/anie.202301601
Aberle, Benjamin, Kowalczyk, Daniel, Massini, Simon, Egler-Kemmerer, Alexander-Nicholas, Gergel, Sebastian, Hammer, Stephan, and Hauer, Bernhard. 2023. “Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids”. Angewandte Chemie International Edition 62 (26): e202301601.
Aberle, B., Kowalczyk, D., Massini, S., Egler-Kemmerer, A. - N., Gergel, S., Hammer, S., and Hauer, B. (2023). Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids. Angewandte Chemie International Edition 62:e202301601.
Aberle, B., et al., 2023. Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids. Angewandte Chemie International Edition, 62(26): e202301601.
B. Aberle, et al., “Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids”, Angewandte Chemie International Edition, vol. 62, 2023, : e202301601.
Aberle, B., Kowalczyk, D., Massini, S., Egler-Kemmerer, A.-N., Gergel, S., Hammer, S., Hauer, B.: Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids. Angewandte Chemie International Edition. 62, : e202301601 (2023).
Aberle, Benjamin, Kowalczyk, Daniel, Massini, Simon, Egler-Kemmerer, Alexander-Nicholas, Gergel, Sebastian, Hammer, Stephan, and Hauer, Bernhard. “Methylation of Unactivated Alkenes with Engineered Methyltransferases To Generate Non‐natural Terpenoids”. Angewandte Chemie International Edition 62.26 (2023): e202301601.
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