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Issue 30, 2016
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Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH

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Abstract

The bis(2-sulfanylethyl)amide (SEA) N,S-acyl shift thioester surrogate has found a variety of useful applications in the field of protein total synthesis. Here we present novel insights into the SEA amide/thioester equilibrium in water which is an essential step in any reaction involving the thioester surrogate properties of the SEA group. We also show that the SEA amide thioester equilibrium can be efficiently displaced at neutral pH for accessing peptide alkylthioesters, i.e. the key components of the native chemical ligation (NCL) reaction.

Graphical abstract: Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH

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Publication details

The article was received on 17 May 2016, accepted on 01 Jun 2016 and first published on 02 Jun 2016


Article type: Paper
DOI: 10.1039/C6OB01079B
Citation: Org. Biomol. Chem., 2016,14, 7211-7216
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    Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH

    S. L. Pira, O. El Mahdi, L. Raibaut, H. Drobecq, J. Dheur, E. Boll and O. Melnyk, Org. Biomol. Chem., 2016, 14, 7211
    DOI: 10.1039/C6OB01079B

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