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Thioether
About: Thioether is a research topic. Over the lifetime, 4320 publications have been published within this topic receiving 63410 citations.
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TL;DR: A unique structural feature at the copper site with a novel thioether bond linking Cys 228 and Tyr 272 in a stacking interaction with Trp 290 is revealed, which may represent a new mechanism for mediating electron transfer in metalloenzymes in the absence of exogenous cofactors.
Abstract: Galactose oxidase is an extracellular enzyme secreted by the fungus Dactylium dendroides. It is monomeric, with a relative molecular mass of 68,000, catalyses the stereospecific oxidation of a broad range of primary alcohol substrates and possesses a unique mononuclear copper site essential for catalysing a two-electron transfer reaction during the oxidation of primary alcohols to corresponding aldehydes. Recent evidence arguing against a Cu(III)-Cu(I) couple implies the existence of a second redox-active site proposed to involve pyrroloquinoline quinone or a tyrosine radical. We now report the crystal structure of galactose oxidase at 1.7 A resolution. This reveals a unique structural feature at the copper site with a novel thioether bond linking Cys 228 and Tyr 272 in a stacking interaction with Trp 290. We propose that these molecular components stabilize the protein free-radical species essential for catalysis and thus provide a 'built-in' secondary cofactor. This feature may represent a new mechanism for mediating electron transfer in metalloenzymes in the absence of exogenous cofactors.
692 citations
TL;DR: The three-dimensional structure of plastocyanin, a blue or "Type 1" copper-protein, has been determined at a resolution of 2.7 A as discussed by the authors, and it is coordinated by a cysteine thiol group, a methionine thioether group and two histidine imidazole groups.
Abstract: The three-dimensional structure of plastocyanin, a ‘blue’ or ‘Type 1’ copper-protein, has been determined at a resolution of 2.7 A. The copper atom has a highly distorted tetrahedral coordination geometry. It is coordinated by a cysteine thiol group, a methionine thioether group, and two histidine imidazole groups.
666 citations
TL;DR: The data indicate that new linkers can be obtained with improved in vivo stability by replacing the maleimide with an acetamide, but the resulting ADCs had similar tolerability and activity profiles.
445 citations
TL;DR: It is shown that the resulting succinimide thioether formed by the Michael-type addition of thiols to N-ethylmaleimide, generally accepted as stable, undergoes retro and exchange reactions in the presence of other thiol compounds at physiological pH and temperature, offering a novel strategy for controlled release.
351 citations
TL;DR: In this paper, a summary of the coordination chemistry of homoleptic thioether macrocycles is presented, with emphasis on likely future developments and uses, and some unpublished results are discussed.
Abstract: Publisher Summary This chapter presents a summary that discusses the coordination chemistry of homoleptic thioether macrocycles critically, with emphasis on likely future developments and uses. Some unpublished results, mainly crystallographic data from laboratories, are discussed in this chapter. The coordination chemistry of thioether ligands has undergone a renaissance over the past five years. This has been because of the observation that cyclic thioethers can bind to a range of transition metal ions to form stable metal complexes. The properties of the M-S(thioether) bond can now be studied with a variety of metal centers, oxidation states, and coordination geometries. Another impetus for the study of the coordination chemistry of crown thioethers stems from the role of thioether binding in biological systems, such as d-biotin (involving tetrahydrothiophene), and blue copper proteins, such as plastocyanin and azurin (involving methionine). The high-yield syntheses of macrocyclic polyoxoethers are characterized by the strong template effects that arise from oxygen coordination by alkali metal ions during cyclization of polyoxo units. The parallel between the binding of soft transition metal ions by soft cyclic thioether ligands and the binding of hard main-group metal ions (Group IA and IIA) by hard cyclic oxyether ligands is presented.
280 citations