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Please use this identifier to cite or link to this item: https://doi.org/10.21256/zhaw-23939
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dc.contributor.authorEichenberger, Michael-
dc.contributor.authorHüppi, Sean-
dc.contributor.authorPatsch, David-
dc.contributor.authorAeberli, Natalie-
dc.contributor.authorBerweger, Raphael-
dc.contributor.authorDossenbach, Sandro-
dc.contributor.authorEichhorn, Eric-
dc.contributor.authorFlachsmann, Felix-
dc.contributor.authorHortencio, Lucas-
dc.contributor.authorVoirol, Francis-
dc.contributor.authorVollenweider, Sabine-
dc.contributor.authorBornscheuer, Uwe T.-
dc.contributor.authorBuller, Rebecca-
dc.date.accessioned2022-01-20T09:44:46Z-
dc.date.available2022-01-20T09:44:46Z-
dc.date.issued2021-
dc.identifier.issn1433-7851de_CH
dc.identifier.issn1521-3773de_CH
dc.identifier.urihttps://digitalcollection.zhaw.ch/handle/11475/23939-
dc.description.abstractSqualene-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.de_CH
dc.language.isoende_CH
dc.publisherWileyde_CH
dc.relation.ispartofAngewandte Chemie: International Editionde_CH
dc.rightshttp://creativecommons.org/licenses/by/4.0/de_CH
dc.subjectChemoenzymatic synthesisde_CH
dc.subjectCyclizationde_CH
dc.subjectProtein engineeringde_CH
dc.subjectSqualene-hopene cyclasede_CH
dc.subjectSubstrate engineeringde_CH
dc.subject.ddc660: Technische Chemiede_CH
dc.titleAsymmetric cation-olefin monocyclization by engineered squalene-hopene cyclasesde_CH
dc.typeBeitrag in wissenschaftlicher Zeitschriftde_CH
dcterms.typeTextde_CH
zhaw.departementLife Sciences und Facility Managementde_CH
zhaw.organisationalunitInstitut für Chemie und Biotechnologie (ICBT)de_CH
dc.identifier.doi10.1002/anie.202108037de_CH
dc.identifier.doi10.21256/zhaw-23939-
dc.identifier.pmid34346556de_CH
zhaw.funding.euNode_CH
zhaw.issue50de_CH
zhaw.originated.zhawYesde_CH
zhaw.pages.end26086de_CH
zhaw.pages.start26080de_CH
zhaw.publication.statuspublishedVersionde_CH
zhaw.volume60de_CH
zhaw.publication.reviewPeer review (Publikation)de_CH
zhaw.webfeedBiokatalysede_CH
zhaw.funding.zhawBiocatalytic Production - Engineering of terpene cyclases for the production of R-alpha-Iononede_CH
zhaw.author.additionalNode_CH
zhaw.display.portraitYesde_CH
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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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