1364705-87-2

Upstream product

• 71400-64-1 (S)-methyl 2-amino-3-(4-(benzyloxy)-3-iodophenyl)propanoate hydrochloride 
• 100-39-0 benzyl bromide 
• 70-78-0 3-Iodo-L-tyrosine 
• 1364705-24-7 (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid 
• 108-24-7 acetic anhydride 
• 1364705-71-4 (6S,9S,12S)-methyl 12-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9-tetramethyl-4,7,10-trioxo-3-oxa-5,8,11-triazatridecan-13-oate 
• 1364705-39-4 (S)-methyl 3-(4-(benzyloxy)-3-iodophenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 
• 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 

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.