1364707-56-1Relevant articles and documents
Biaryl-bridged macrocyclic peptides: Conformational constraint via carbogenic fusion of natural amino acid side chains
Meyer, Falco-Magnus,Collins, James C.,Borin, Brendan,Bradow, James,Liras, Spiros,Limberakis, Chris,Mathiowetz, Alan M.,Philippe, Laurence,Price, David,Song, Kun,James, Keith
experimental part, p. 3099 - 3114 (2012/05/20)
A general method for constraining peptide conformations via linkage of aromatic sidechains has been developed. Macrocyclization of suitably functionalized tri-, tetra- and pentapeptides via Suzuki-Miyaura cross-coupling has been used to generate side chain to side chain, biaryl-bridged 14- to 21-membered macrocyclic peptides. Biaryl bridges possessing three different configurations, meta-meta, meta-ortho, and ortho-meta, were systematically explored through regiochemical variation of the aryl halide and aryl boronate coupling partners, allowing fine-tuning of the resultant macrocycle conformation. Suzuki-Miyaura macrocyclizations were successfully achieved both in solution and on solid phase for all three sizes of peptide. This approach constitutes a means of constraining peptide conformation via direct carbogenic fusion of side chains of naturally occurring amino acids such as phenylalanine and tyrosine, and so is complementary to strategies involving non-natural, for example, hydrocarbon, bridges.