Simultaneous synthesis of thioesters and iron-sulfur clusters in water: two universal components of energy metabolism

Thioesters are important intermediates in both synthetic organic and biosynthetic reaction pathways. Here we show that thioesters can be synthesized in an aqueous reaction between thioacetate and thiols. The reaction can be coupled to a second reaction between sulfide and either ferrous or ferric ir...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-10, Vol.56 (8), p.11989-11992
Main Authors: Sanden, Sebastian A, Yi, Ruiqin, Hara, Masahiko, McGlynn, Shawn E
Format: Article
Language:English
Subjects:
Clusters
Energy Metabolism - physiology
Iron
Iron - chemistry
Metabolism
Oxidation-Reduction
Peptides - chemistry
Pyruvic Acid - chemistry
Sulfhydryl Compounds - chemistry
Sulfides - chemistry
Sulfur Compounds - chemical synthesis
Temperature
Thioesters
Thiols
Time Factors
Water
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Summary:Thioesters are important intermediates in both synthetic organic and biosynthetic reaction pathways. Here we show that thioesters can be synthesized in an aqueous reaction between thioacetate and thiols. The reaction can be coupled to a second reaction between sulfide and either ferrous or ferric iron, which drives the reaction forward. We furthermore demonstrate that sulfide released during thioester formation can be used in the synthesis of peptide bound [Fe-S] clusters, which like thioesters, are ancient components of metabolism. Together our results reveal a primordial linkage between high-energy ester formation and redox chemistry. Thioesters and peptide ligated [Fe-S] clusters can be synthesized simultaneously from thioacetic acid in an aqueous one-pot reaction.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04078a