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Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology

Author

Listed:
  • Helen M. Burke

    (School of Chemistry, Trinity College Dublin)

  • Lauren McSweeney

    (School of Chemistry, Trinity College Dublin)

  • Eoin M. Scanlan

    (School of Chemistry, Trinity College Dublin)

Abstract

S-to-N acyl transfer is a high-yielding chemoselective process for amide bond formation. It is widely utilized by chemists for synthetic applications, including peptide and protein synthesis, chemical modification of proteins, protein-protein ligation and the development of probes and molecular machines. Recent advances in our understanding of S-to-N acyl transfer processes in biology and innovations in methodology for thioester formation and desulfurization, together with an extension of the size of cyclic transition states, have expanded the boundaries of this process well beyond peptide ligation. As the field develops, this chemistry will play a central role in our molecular understanding of Biology.

Suggested Citation

  • Helen M. Burke & Lauren McSweeney & Eoin M. Scanlan, 2017. "Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology," Nature Communications, Nature, vol. 8(1), pages 1-16, August.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms15655
    DOI: 10.1038/ncomms15655
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    Cited by:

    1. Anupam Prasoon & Xiaoqing Yu & Mike Hambsch & David Bodesheim & Kejun Liu & Angelica Zacarias & Nguyen Ngan Nguyen & Takakazu Seki & Aerzoo Dianat & Alexander Croy & Gianaurelio Cuniberti & Philippe F, 2023. "Site-selective chemical reactions by on-water surface sequential assembly," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Dan Ye & Hong Lu & Yi He & Zhaojing Zheng & Jinghao Wu & Hao Wei, 2022. "Rapid syntheses of N-fused heterocycles via acyl-transfer in heteroaryl ketones," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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