Peptide Weinreb amide derivatives as thioester precursors for native chemical ligation. Issue 12 (7th February 2017)

• Record Type: Journal Article
• Authors: Rao, Chang; Liu, Chuan-Fa
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 12(2017)
• Page Start: 2491
• Page End: 2496
• Publication Date: 2017-02-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00103g
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Peptide C-ter Weinreb amide derivatives are excellent thioester surrogates for native chemical ligation. Abstract : Peptide Weinreb amide derivatives with an N -substituted mercaptoethyl group are designed as thioester precursors for native chemical ligation. We show that these amides undergo rapid ligation with a cysteinyl peptide under normal NCL conditions to form various Xaa–Cys peptide bonds, including the difficult Val–Cys junction. Facile synthesis of the Weinreb amide linkers allows easy access to this new type of peptide thioester precursor by standard Fmoc solid phase synthesis.