Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki reaction.
[reaction: see text] Since peroxidase-catalyzed dityrosine formation is inefficient for peptides, we have developed alternative conditions for intermolecular dityrosine formation using the Miyaura-Suzuki reaction. A one-pot reaction is effective for cross-linking short peptides, but longer peptides inhibit the Suzuki step, mandating a traditional two-step procedure using potassium acetate for the Miyaura reaction and potassium carbonate for the Suzuki coupling. These palladium-based methods are complementary to the well-established peroxidase-catalyzed oxidative phenolic coupling of full-length proteins.
Yoburn
Joshua C
JC
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Van Vranken
David L
DL
D019281:Dimerization; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry*
D010455:Peptides; D014443:Tyrosine; C007543:dityrosine