Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation

Zheng, J.-S.; Chang, H.-N.; Wang, F.-L.; Liu, L.

Journal of the American Chemical Society 133(29): 11080-11083


ISSN/ISBN: 1520-5126
PMID: 21714552
DOI: 10.1021/ja204088a
Accession: 053270566

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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.