ArticleOrganic letters2025
Biocatalytic Thioketal Cleavage Enabled by Enzymatic Bromide Recycling by Vanadium-Dependent Haloperoxidases.
Article in Organic letters, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Biocatalytic Synthesis of Isoxazolines Enabled by Cryptic Nitrile Oxide Formation by a Vanadium-Dependent Chloroperoxidase.Angewandte Chemie (International ed. in English) · 2026Article
- Chemoenzymatic Triazolopyridine Synthesis Enabled by Cryptic Diazo Formation by Vanadium-Dependent Haloperoxidases.Organic letters · 2026Article
- Oxidative Rearrangement of Indoles Enabled by Promiscuous Cryptic Halogenation with Vanadium-Dependent Haloperoxidases.ACS catalysis · 2026Article
- Chemoenzymatic Diazo Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases.Journal of the American Chemical Society · 2026Article
- Peptide halogenation biochemistry: interfacing pharmaceutical deliverables with chemical innovation.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2025Review
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3 authors.
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Abstract
Thioketals are an important class of molecules used for the preparation and protection of carbonyl compounds in chemical synthesis. Selective cleavage of thioketals requires the use of harsh conditions and reagents that limit the use of thioketals in chemoenzymatic synthesis. Herein, we describe a biocatalytic strategy for the cleavage of thioketals using enzymatic bromide recycling by vanadium-dependent haloperoxidase (VHPO) enzymes. This reaction design involves halogenation-mediated thioketal cleavage through repetitive enzyme-mediated formation of hypobromous acid with a catalytic quantity of bromide salt and hydrogen peroxide as the terminal oxidant. This protocol is demonstrated on a broad range of 1,3-dithiolanes in high yield and excellent chemoselectivity, performed on a gram scale, run with lysate and whole cells, and applied to the cleavage of 1,3-dithianes and 1,3-oxathiolanes.
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