ArticleAngewandte Chemie (International ed. in English)2021
Stereoselective Directed Cationic Cascades Enabled by Molecular Anchoring in Terpene 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 10 papers.
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Who cites it
10 citing papers in PubMed.
- Catalytic Asymmetric Cationic Geranyl Cyclizations.Journal of the American Chemical Society · 2026Article
- Review
- Biocatalytic stereocontrolled head-to-tail cyclizations of unbiased terpenes as a tool in chemoenzymatic synthesis.Nature communications · 2024Article
- Recent Developments and Applications of Biocatalytic and Chemoenzymatic Synthesis for the Generation of Diverse Classes of Drugs.Current pharmaceutical biotechnology · 2024Article
- A Concise Diastereoselective Total Synthesis of α-Ambrinol.Marine drugs · 2023Article
- Spheroplasts preparation boosts the catalytic potential of a squalene-hopene cyclase.Nature communications · 2022Article
- Recent Advances in Biocatalysis for Drug Synthesis.Biomedicines · 2022Review
- New Trends and Future Opportunities in the Enzymatic Formation of C-C, C-N, and C-O bonds.Chembiochem : a European journal of chemical biology · 2022Review
- Asymmetric Cation-Olefin Monocyclization by Engineered Squalene-Hopene Cyclases.Angewandte Chemie (International ed. in English) · 2021Article
- Stereoselective Directed Cationic Cascades Enabled by Molecular Anchoring in Terpene Cyclases.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cascade reactions appeared as a cutting-edge strategy to streamline the assembly of complex structural scaffolds from naturally available precursors in an atom-, as well as time, labor- and cost-efficient way. We herein report a strategy to control cationic cyclization cascades by exploiting the ability of anchoring dynamic substrates in the active site of terpene cyclases via designed hydrogen bonding. Thereby, it is possible to induce "directed" cyclizations in contrast to established "non-stop" cyclizations (99:1) and predestinate cascade termination at otherwise catalytically barely accessible intermediates. As a result, we are able to provide efficient access to naturally widely occurring apocarotenoids, value-added flavors and fragrances in gram-scale by replacing multi-stage synthetic routes to a single step with unprecedented selectivity (>99.5 % ee) and high yields (up to 89 %).
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.