Selective Stepwise Arylation of Unprotected Peptides by PtIV Complexes. (2nd June 2022)

• Record Type: Journal Article
• Authors: Lin, Xiaoxi; Haimov, Elvira; Redko, Boris; Vigalok, Arkadi
• Is Part Of: Angewandte Chemie. Volume 134:Number 29(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-02
• Subjects: Arylation Reactions -- Bioconjugation -- Peptides -- Platinum Complexes; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202205368
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: LPt IV F(Aryl) complexes bearing a bulky bidentate 2‐[bis(adamant‐1‐yl)phosphino]phenoxide ligand (L) demonstrate excellent reactivity and selectivity in the arylation of X−H (X=S, N) bonds of amino acid residues in unprotected peptides under mild, including aqueous, conditions. Stepwise addition of these complexes allowed a convenient one‐pot introduction of different aromatic groups in the X−H bonds of Cys and N terminus. Pt IV reagents can also be used to further arylate N−H bonds in Lys and Trp providing access to peptides bearing multiple aromatic groups. Abstract : A selective stepwise arylation of S−H and N−H bonds in unprotected peptides by air‐ and moisture‐ stable Pt IV complexes is reported. These compounds showed high reactivity and selectivity toward the N terminal NH2 group over other N−H bonds in complex biologically relevant substrates.