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Peptide/Protein Stapling and Unstapling: Introduction of s -Tetrazine, Photochemical Release, and Regeneration of the Peptide/Protein

2015; American Chemical Society; Volume: 137; Issue: 12 Linguagem: Inglês

10.1021/ja512880g

1943-2984

Stephen P. Brown, Amos B. Smith,

Monoclonal and Polyclonal Antibodies Research

Protocols have been achieved that permit facile introduction of s-tetrazine into unprotected peptides and the protein, thioredoxin, between two cysteine sulfhydryl groups (i.e., staple), followed by photochemical release (i.e., unstaple) and regeneration of the peptide/protein upon removal of the cyano groups from the derived bisthiocyanate. The S,S-tetrazine macrocycles in turn provide a convenient handle for probe introduction by exploiting the inverse electron demand Diels–Alder reactivity of the tetrazine.