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https://doi.org/10.21256/zhaw-23939| Publikationstyp: | Beitrag in wissenschaftlicher Zeitschrift |
| Art der Begutachtung: | Peer review (Publikation) |
| Titel: | Asymmetric cation-olefin monocyclization by engineered squalene-hopene cyclases |
| Autor/-in: | Eichenberger, Michael Hüppi, Sean Patsch, David Aeberli, Natalie Berweger, Raphael Dossenbach, Sandro Eichhorn, Eric Flachsmann, Felix Hortencio, Lucas Voirol, Francis Vollenweider, Sabine Bornscheuer, Uwe T. Buller, Rebecca |
| et. al: | No |
| DOI: | 10.1002/anie.202108037 10.21256/zhaw-23939 |
| Erschienen in: | Angewandte Chemie: International Edition |
| Band(Heft): | 60 |
| Heft: | 50 |
| Seite(n): | 26080 |
| Seiten bis: | 26086 |
| Erscheinungsdatum: | 2021 |
| Verlag / Hrsg. Institution: | Wiley |
| ISSN: | 1433-7851 1521-3773 |
| Sprache: | Englisch |
| Schlagwörter: | Chemoenzymatic synthesis; Cyclization; Protein engineering; Squalene-hopene cyclase; Substrate engineering |
| Fachgebiet (DDC): | 660: Technische Chemie |
| Zusammenfassung: | Squalene-hopene cyclases (SHCs) have great potential for the industrial synthesis of enantiopure cyclic terpenoids. A limitation of SHC catalysis has been the enzymes' strict (S)-enantioselectivity at the stereocenter formed after the first cyclization step. To gain enantio-complementary access to valuable monocyclic terpenoids, an SHC-wild-type library including 18 novel homologs was set up. A previously not described SHC (AciSHC) was found to synthesize small amounts of monocyclic (R)-γ-dihydroionone from (E/Z)-geranylacetone. Using enzyme and process optimization, the conversion to the desired product was increased to 79 %. Notably, analyzed AciSHC variants could finely differentiate between the geometric geranylacetone isomers: While the (Z)-isomer yielded the desired monocyclic (R)-γ-dihydroionone (>99 % ee), the (E)-isomer was converted to the (S,S)-bicyclic ether (>95 % ee). Applying the knowledge gained from the observed stereodivergent and enantioselective transformations to an additional SHC-substrate pair, access to the complementary (S)-γ-dihydroionone (>99.9 % ee) could be obtained. |
| URI: | https://digitalcollection.zhaw.ch/handle/11475/23939 |
| Volltext Version: | Publizierte Version |
| Lizenz (gemäss Verlagsvertrag): | CC BY 4.0: Namensnennung 4.0 International |
| Departement: | Life Sciences und Facility Management |
| Organisationseinheit: | Institut für Chemie und Biotechnologie (ICBT) |
| Publiziert im Rahmen des ZHAW-Projekts: | Biocatalytic Production - Engineering of terpene cyclases for the production of R-alpha-Ionone |
| Enthalten in den Sammlungen: | Publikationen Life Sciences und Facility Management |
Dateien zu dieser Ressource:
| Datei | Beschreibung | Größe | Format | |
|---|---|---|---|---|
| 2021_Eichenberger-etal_Asymmetric-Monocyclization_AngewChemInt.pdf | 2.77 MB | Adobe PDF |  Öffnen/Anzeigen |
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Eichenberger, M., Hüppi, S., Patsch, D., Aeberli, N., Berweger, R., Dossenbach, S., Eichhorn, E., Flachsmann, F., Hortencio, L., Voirol, F., Vollenweider, S., Bornscheuer, U. T., & Buller, R. (2021). Asymmetric cation-olefin monocyclization by engineered squalene-hopene cyclases. Angewandte Chemie: International Edition, 60(50), 26080–26086. https://doi.org/10.1002/anie.202108037
Eichenberger, M. et al. (2021) ‘Asymmetric cation-olefin monocyclization by engineered squalene-hopene cyclases’, Angewandte Chemie: International Edition, 60(50), pp. 26080–26086. Available at: https://doi.org/10.1002/anie.202108037.
M. Eichenberger et al., “Asymmetric cation-olefin monocyclization by engineered squalene-hopene cyclases,” Angewandte Chemie: International Edition, vol. 60, no. 50, pp. 26080–26086, 2021, doi: 10.1002/anie.202108037.
EICHENBERGER, Michael, Sean HÜPPI, David PATSCH, Natalie AEBERLI, Raphael BERWEGER, Sandro DOSSENBACH, Eric EICHHORN, Felix FLACHSMANN, Lucas HORTENCIO, Francis VOIROL, Sabine VOLLENWEIDER, Uwe T. BORNSCHEUER und Rebecca BULLER, 2021. Asymmetric cation-olefin monocyclization by engineered squalene-hopene cyclases. Angewandte Chemie: International Edition. 2021. Bd. 60, Nr. 50, S. 26080–26086. DOI 10.1002/anie.202108037
Eichenberger, Michael, Sean Hüppi, David Patsch, Natalie Aeberli, Raphael Berweger, Sandro Dossenbach, Eric Eichhorn, et al. 2021. “Asymmetric Cation-Olefin Monocyclization by Engineered Squalene-Hopene Cyclases.” Angewandte Chemie: International Edition 60 (50): 26080–86. https://doi.org/10.1002/anie.202108037.
Eichenberger, Michael, et al. “Asymmetric Cation-Olefin Monocyclization by Engineered Squalene-Hopene Cyclases.” Angewandte Chemie: International Edition, vol. 60, no. 50, 2021, pp. 26080–86, https://doi.org/10.1002/anie.202108037.
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