Intermolecular 1,2,4-Thiadiazole Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

The enzymatic synthesis of heterocycles is an emerging biotechnology for the sustainable construction societally important molecules. Herein, we describe enzyme-mediated strategy oxidative dimerization thioamides enabled by halide recycling vanadium-dependent haloperoxidase enzymes. This approach allows intermolecular biocatalytic bond formation using a catalytic quantity salt and hydrogen peroxide as terminal oxidant. established method applied to diverse range generate corresponding 1,2,4-thiadiazoles in moderate high yields with excellent chemoselectivity. Mechanistic experiments suggest that reaction proceeds through two distinct sulfur halogenation events are critical heterocycle formation. Molecular docking provide insight into reactivity differences between biocatalysts used this study. Finally, developed preparative scale chemoenzymatic anticancer agent penicilliumthiamine B. These studies demonstrate promising platform

Language: Английский

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Electrochemical Organic Synthesis

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2797 - 2798

Published: Aug. 29, 2023

Received: 03 August 2023 Accepted after revision: Article published online:29

Language: Английский

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Electrochemical Construction of C–S Bond: A Green Approach for Preparing Sulfur-Containing Scaffolds

Pharmaceutical Fronts, Journal Year: 2024, Volume and Issue: 06(01), P. e9 - e19

Published: March 1, 2024

Abstract The organosulfur frameworks containing C–S bonds are important structural motifs in various biologically active molecules and functional materials. In this regard, transition-metal catalysis using chemical oxidants to prime reactions has emerged as the most common method, however, is prone several side such dimerization overoxidation. recent years, organic electrosynthesis become a hot topic due its eco-friendly mild process which costly catalysts toxic could be replaced by electrons. This perspective summarized recently developed bond protocols, discussing highlighting reaction features, substrate scope, well application pharmaceuticals, underlying mechanisms. study helps development of electrochemical process-enabled construction future.

Language: Английский

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Metal Complexes with Redox-Active Ligands in the Indirect Electrosynthesis of Organic Sulfur Compounds

Russian Journal of Coordination Chemistry, Journal Year: 2023, Volume and Issue: 49(S2), P. S128 - S158

Published: Dec. 1, 2023

Language: Английский

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