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Dynamic Phosphorus: Thiolate Exchange Cascades with Higher Phosphorothioates

Published inAngewandte Chemie, vol. 62, no. 51, e202313931
Publication date2023-11-21
First online date2023-11-21
Abstract

Abstract

In this study, we introduce phosphorus, a pnictogen, as an exchange center for dynamic covalent chemistry. Cascade exchange of neutral phosphorotri‐ and ‐tetrathioates with thiolates is demonstrated in organic solvents, aqueous micellar systems, and in living cells. Exchange rates increase with the pH value, electrophilicity of the exchange center, and nucleophilicity of the exchangers. Molecular walking of the dynamic phosphorus center along Hammett gradients is simulated by the sequential addition of thiolate exchangers. Compared to phosphorotrithioates, tetrathioates are better electrophiles with higher exchange rates. Dynamic phosphorotri‐ and ‐tetrathioates are non‐toxic to HeLa Kyoto cells and participate in the dynamic networks that account for thiol‐mediated uptake into living cells.

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BOUFFARD, Jules et al. Dynamic Phosphorus: Thiolate Exchange Cascades with Higher Phosphorothioates. In: Angewandte Chemie, 2023, vol. 62, n° 51, p. e202313931. doi: 10.1002/anie.202313931
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ISSN of the journal1433-7851
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