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

ABSTRACT: 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 chain with the side group of serine. The activated cyclic urethane moiety undergoes displacement by a thiol to generate the thioester directly from the solid support. Importantly, the method activates the serine residue for the synthesis of peptide thioesters; thus it is fully automated and free of the types of resins, linkers, handles, and unnatural amino acids typically needed for the s

SUBMITTER: Elashal HE 

PROVIDER: S-EPMC5308276 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature