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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Autor*in
Aberle, Benjamin;
Kowalczyk, Daniel;
Massini, Simon;
Egler-Kemmerer, Alexander-Nicholas;
Gergel, SebastianUniBi;
Hammer, StephanUniBi ;
Hauer, Bernhard
Einrichtung
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
Urheberrecht / Lizenzen
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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