Selective Stepwise Arylation of Unprotected Peptides by PtIV Complexes

Xiaoxi Lin, Elvira Haimov, Boris Redko, Arkadi Vigalok*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

LPtIVF(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. PtIV reagents can also be used to further arylate N−H bonds in Lys and Trp providing access to peptides bearing multiple aromatic groups.

Original languageEnglish
Article numbere202205368
JournalAngewandte Chemie - International Edition
Volume61
Issue number29
DOIs
StatePublished - 18 Jul 2022

Funding

FundersFunder number
Jerusalem, Israel and Joint NSFC‐ISF2572/17
NSFC-ISF
United States-Israel Binational Science Foundation2014254

    Keywords

    • Arylation Reactions
    • Bioconjugation
    • Peptides
    • Platinum Complexes

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