A straightforward method for automated Fmoc-based synthesis of bio-inspired peptide crypto-thioesters

Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation† †Electronic supplementary information (ESI) available: Experimental procedures and analytical data for new compounds. See DOI: 10.1039/c6sc02162j Click here for additional data file.

Fmoc solid phase peptide synthesis of thioesters for the chemical synthesis of proteins via native chemical ligation is a challenge. We have developed a versatile approach for direct synthesis of peptide thioesters from a solid support utilizing Fmoc chemistry. Peptide thioester synthesis is performed by the formation of a cyclic urethane moiety via a selective reaction of the backbone amide ch...

Serine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation.

Fmoc solid phase peptide synthesis of thioesters for the chemical synthesis of proteins via native chemical ligation is a challenge. We have developed a versatile approach for direct synthesis of peptide thioesters from a solid support utilizing Fmoc chemistry. Peptide thioester synthesis is performed by the formation of a cyclic urethane moiety via a selective reaction of the backbone amide ch...

Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer

Peptide thioester synthesis by N→S acyl transfer is being intensively explored by many research groups the world over. Reasons for this likely include the often straightforward method of precursor assembly using Fmoc-based chemistry and the fundamentally interesting acyl migration process. In this review we introduce recent advances in this exciting area and discuss, in more detail, our own eff...

Fmoc-Compatible Solid Phase Peptide Synthesis of Long C-Terminal Peptide Thioesters

Advances in Fmoc solid‐phase peptide synthesis

Today, Fmoc SPPS is the method of choice for peptide synthesis. Very-high-quality Fmoc building blocks are available at low cost because of the economies of scale arising from current multiton production of therapeutic peptides by Fmoc SPPS. Many modified derivatives are commercially available as Fmoc building blocks, making synthetic access to a broad range of peptide derivatives straightforwa...