1364705-24-7

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 942070-92-0 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate 
• 851967-77-6 methyl (2S)-3-(3-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 

Downstream Products

• 1364705-47-4 Boc-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 
• 1364705-55-4 Ac-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 
• 1364705-79-2 Boc-(cyclo-m,m)-[(3-Cl)FAAY]-CO₂Me 
• 1364705-87-2 Ac-(cyclo-m,m)-[(3-Cl)FAAY]-CO₂Me 
• 1364706-10-4 Boc-(cyclo-m,m)-[(3-Cl)FAAAY]-CO₂Me 
• 1364706-18-2 Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO₂Me 

Relevant academic research and scientific papers

Biaryl-bridged macrocyclic peptides: Conformational constraint via carbogenic fusion of natural amino acid side chains

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.