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Org Lett. 2016 Nov 18;18(22):5940-5943. Epub 2016 Nov 2.

N-Sulfanylethylaminooxybutyramide (SEAoxy): A Crypto-Thioester Compatible with Fmoc Solid-Phase Peptide Synthesis.

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Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University , Tokushima 770-8505, Japan.


An N-sulfanylethylaminooxybutyramide (SEAoxy) has been developed as a novel thioester equivalent for native chemical ligation. SEAoxy peptide was straightforwardly synthesized by conventional Fmoc solid-phase peptide synthesis without a problem. Moreover, SEAoxy peptide could be directly applied to native chemical ligation owing to the intramolecular N-to-S acyl shift that releases the peptide-thioester in situ. This methodology was successfully applied to the synthesis of two bioactive peptides.

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