1417697-56-3Relevant academic research and scientific papers
Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
Afonso, Ana,Cusso, Olaf,Feliu, Lidia,Planas, Marta
, p. 6204 - 6211 (2013/01/15)
A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe-Tyr or a Tyr-Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted Suzuki-Miyaura reaction for the formation of the macrocycle. First, the feasibility of the solid-phase Miyaura borylation of a 3-iodotyrosyltripeptide was established. Then, the Suzuki-Miyaura reaction was applied to the cross-coupling of linear 3-boronotyrosine-containing peptidyl resins with iodobenzene and with halogenated aromatic amino acids. Finally, this methodology was extended to the synthesis of biaryl cyclic peptides through the preparation of a linear peptidyl resin containing both the required boronate and halogenated derivatives, followed by a microwave-assisted Suzuki-Miyaura macrocyclization.
