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Kang, H. Thioester Synthesis. Encyclopedia. Available online: https://encyclopedia.pub/entry/60880 (accessed on 23 October 2026).
Kang H. Thioester Synthesis. Encyclopedia. Available at: https://encyclopedia.pub/entry/60880. Accessed October 23, 2026.
Kang, Helena. "Thioester Synthesis" Encyclopedia, https://encyclopedia.pub/entry/60880 (accessed October 23, 2026).
Kang, H. (2026, October 12). Thioester Synthesis. In Encyclopedia. https://encyclopedia.pub/entry/60880
Kang, Helena. "Thioester Synthesis." Encyclopedia. Web. 12 October, 2026.

Thioester Synthesis

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Thioester synthesis comprises transformations that form compounds of general structure R–C(=O)–S–R′, where sulfur replaces the alkoxy oxygen of an ordinary ester. The defining bond-forming event is acyl–sulfur bond formation, most directly achieved by reaction of a thiol or thiolate with an activated carboxylic-acid derivative. Carboxylic acids may first be converted into acyl chlorides, anhydrides, activated esters, or coupling-reagent intermediates; alternative catalytic routes include dehydrogenative coupling of alcohols with thiols and carbonylative processes [1]. Thioesters retain an acyl carbonyl and undergo nucleophilic acyl substitution because sulfur provides weaker resonance donation than oxygen. They are distinct from sulfides, which lack a carbonyl adjacent to sulfur, and from thiocarboxylic acids, R–C(=O)–SH. In chemoselective ligation, a peptide thioester undergoes transthioesterification and S-to-N acyl transfer, illustrating that the thioester is an activated acyl donor rather than simply a sulfur-substituted ether [2].

thioester synthesis acyl transfer thiol acylation native chemical ligation
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References

  1. Xuewei Wang; Yongli Zhao; Jinhua Yang; Yanxi Li; Ying Luo; Mengyao Xu; Junfeng Zhao; Ynamide-Mediated Thioester Synthesis. J. Org. Chem. 2021, 86, 18265-18277. [CrossRef]
  2. Philip E. Dawson; Tom W. Muir; Ian Clark-Lewis; Stephen B. H. Kent; Synthesis of Proteins by Native Chemical Ligation. Sci. 1994, 266, 776-779. [CrossRef]
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Subjects: Chemistry, Organic
Contributor MDPI registered users' name will be linked to their SciProfiles pages. To register with us, please refer to https://encyclopedia.pub/register : Helena Kang
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Entry Collection: Organic Chemistry
Revision: 1 time (View History)
Update Date: 19 Oct 2026
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