Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds. Issue 4 (8th February 2017)

• Record Type: Journal Article
• Authors: Saito, Fumito; Bode, Jeffrey W.
• Is Part Of: Chemical science. Volume 8:Issue 4(2017)
• Page Start: 2878
• Page End: 2884
• Publication Date: 2017-02-08
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc00021a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Proteolytically stable lasso peptides are formed by grafting peptide epitopes onto peptide-based [1]rotaxanes by dual native chemical ligation and KAHA ligation. Abstract : The chemical synthesis of peptide-based [1]rotaxanes (lasso peptides) was achieved by [2]rotaxane formation followed by two chemoselective ligation reactions. Our approach enabled incorporation of various peptide sequences into a common rotaxane structure. The synthetic lasso peptides were characterized by NMR, chromatography, and partial degradation by proteases. A linear peptide epitope grafted onto the rotaxane scaffold showed significantly improved proteolytic stability.