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Fmoc Synthesis of Peptide Thioesters without Post-Chain-Assembly Manipulation

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journal contribution
posted on 27.07.2011, 00:00 by Ji-Shen Zheng, Hao-Nan Chang, Feng-Liang Wang, Lei Liu
An operationally simple method for the synthesis of peptide thioesters is developed using standard Fmoc solid-phase peptide synthesis procedures. The method relies on the use of a premade enamide-containing amino acid which, in the final TFA cleavage step, renders the desired thioester functionality through an irreversible intramolecular N-to-S acyl transfer.