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.

Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds† †Electronic supplementary information (ESI) available: Experimental procedures and analytical data of all new compounds. CCDC 1520783. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc00021a Click here for additional data file. Click here for additional data file.

Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation† †Electronic supplementary information (ESI) available: Experimental procedures and analytical data of all new compounds. See DOI: 10.1039/c5sc01774b Click here for additional data file.

Optimisation of chemical protein cleavage for erythropoietin semi-synthesis using native chemical ligation† †Electronic supplementary information (ESI) available: MS and LC-MS characterisation for thioester 2 and the M54L EPO mutant. See DOI: 10.1039/b811501j Click here for additional data file.

Selective protein cleavage at methionine residues is a useful method for the production of bacterially derived protein fragments containing an N-terminal cysteine residue required for native chemical ligation. Here we describe an optimised procedure for cyanogen bromide-mediated protein cleavage, and ligation of the resulting fragments to afford biologically active proteins.

3-Mercaptopropionic acid-mediated synthesis of peptide and protein thioesters† †Electronic supplementary information (ESI) available: Experimental procedures for the production of 1, all model peptides and proteins and their reactions with MPA including HPLC, LC-MS and NMR characterisation of selected products. See DOI: 10.1039/b815888f Click here for additional data file.

Peptides and proteins fragment sequence-specifically in the presence of 3-mercaptopropionic acid to afford thioesters which can be used in native chemical ligation reactions.

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...