ArticleAngewandte Chemie (International ed. in English)2021
Asymmetric Cation-Olefin Monocyclization by Engineered Squalene-Hopene Cyclases.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The trial behind it
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Who cites it
8 citing papers in PubMed, 23 citations in OpenAlex.
- Catalytic Asymmetric Cationic Geranyl Cyclizations.Journal of the American Chemical Society · 2026Article
- A tailored CoA ligase-Nature catalysis · 2026Article
- Combining biocatalytic and radical retrosynthesis for efficient chemoenzymatic synthesis of natural products.Chemical Society reviews · 2025Review
- Review
- LibGENiE - A bioinformatic pipeline for the design of information-enriched enzyme libraries.Computational and structural biotechnology journal · 2023Article
- The catalytic role of glutathione transferases in heterologous anthocyanin biosynthesis.Nature catalysis · 2023Article
- Spheroplasts preparation boosts the catalytic potential of a squalene-hopene cyclase.Nature communications · 2022Article
- Asymmetric Cation-Olefin Monocyclization by Engineered Squalene-Hopene Cyclases.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
13 authors at 3 institutions in 3 countries.
Funding
Abstract
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.
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Registered trials
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