ArticleAngewandte Chemie (International ed. in English)2021
Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives.
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 7 papers.
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Who cites it
7 citing papers in PubMed, 17 citations in OpenAlex.
- Nonnative Thiol and Aniline Methylation, Including Enantioselective Dithiol Desymmetrization, by Multicomponent Cobamide-Dependent Methyltransferases Using Unactivated Methyl Donors.Angewandte Chemie (International ed. in English) · 2026Article
- The Expanding Reactivity of Cobamide-Containing Proteins: From Mechanistic Understanding to Non-native Biocatalysis.ACS catalysis · 2026Article
- Non-native Intramolecular Radical Cyclization Catalyzed by a BAngewandte Chemie (International ed. in English) · 2023Article
- Non-Native Site-Selective Enzyme Catalysis.Chemical reviews · 2023Review
- Anaerobic demethylation of guaiacyl-derived monolignols enabled by a designed artificial cobalamin methyltransferase fusion enzyme.RSC advances · 2023Article
- 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
- Thiols Act as Methyl Traps in the Biocatalytic Demethylation of Guaiacol Derivatives.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Demethylating methyl phenyl ethers is challenging, especially when the products are catechol derivatives prone to follow-up reactions. For biocatalytic demethylation, monooxygenases have previously been described requiring molecular oxygen which may cause oxidative side reactions. Here we show that such compounds can be demethylated anaerobically by using cobalamin-dependent methyltransferases exploiting thiols like ethyl 3-mercaptopropionate as a methyl trap. Using just two equivalents of this reagent, a broad spectrum of substituted guaiacol derivatives were demethylated, with conversions mostly above 90 %. This strategy was used to prepare the highly valuable antioxidant hydroxytyrosol on a one-gram scale in 97 % isolated yield.
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Registered trials
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