Fmoc Synthesis of Peptide Thioesters without Post-Chain-Assembly Manipulation
Journal of the American Chemical Society2011Vol. 133(29), pp. 11080–11083
Citations Over TimeTop 10% of 2011 papers
Abstract
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.
Related Papers
- → Solid Phase Synthesis of Peptide C-Terminal Thioesters by Fmoc/t-Bu Chemistry(1999)284 cited
- → Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation(2000)106 cited
- → N-Sulfanylethylaminooxybutyramide (SEAoxy): A Crypto-Thioester Compatible with Fmoc Solid-Phase Peptide Synthesis(2016)18 cited
- → Native Chemical Ligation via N-Acylurea Thioester Surrogates Obtained by Fmoc Solid-Phase Peptide Synthesis(2020)3 cited
- → Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation(2000)3 cited