A thiirane linker for isopeptide mimetics by peptide ligation. Issue 19 (11th May 2016)

• Record Type: Journal Article
• Authors: Kawakami, Toru; Mishima, Yuichi; Kinoshita, Misaki; Lee, Young-Ho; Suetake, Isao
• Is Part Of: Tetrahedron letters. Volume 57:Issue 19(2016)
• Page Start: 2112
• Page End: 2115
• Publication Date: 2016-05-11
• Subjects: CPE ligation -- Histone -- Post-translational modification -- Thiirane -- Ubiquitin; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.006
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A method for introduction of an isopeptide-mimetic structure is proposed. 2-Aminomethylthiirane can be used as a linker for peptide ligation. Ubiquitinated histone proteins can be synthesized. Abstract: 2-Aminomethylthiirane was used to attach a 1, 2-amino-thiol moiety at thiol groups of peptides for use in peptide ligation to produce isopeptide mimetics. To confirm the strategy, a ubiquitinated histone H3 peptide was prepared, and the ubiquitin was correctly folded judging from CD spectra with no influence by the random H3 peptide.