Selective Stepwise Arylation of Unprotected Peptides by PtIV Complexes

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.

Keywords: Arylation Reactions; Bioconjugation; Peptides; Platinum Complexes.