71400-64-1

Upstream product

• 119336-08-2 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate 
• 691394-91-9 methyl (S)-3-(4-(benzyloxy)-3-iodophenyl)-2-((tert-butoxycarbonyl)amino)propanoate 
• 100-39-0 benzyl bromide 
• 70-78-0 3-Iodo-L-tyrosine 
• 67-56-1 methanol 

Downstream Products

• 1373311-92-2 (3S,6S)-3,6-bis(4-(benzyloxy)-3-iodobenzyl)piperazine-2,5-dione 
• 1364706-18-2 Ac-(cyclo-m,m)-[(3-Cl)FAAAY]-CO₂Me 
• 1364706-10-4 Boc-(cyclo-m,m)-[(3-Cl)FAAAY]-CO₂Me 
• 1364706-02-4 (6S,9S,12S,15S)-methyl 15-(4-(benzyloxy)-3-iodobenzyl)-2,2,6,9,12-pentamethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate 
• 1364705-87-2 Ac-(cyclo-m,m)-[(3-Cl)FAAY]-CO₂Me 
• 1364705-79-2 Boc-(cyclo-m,m)-[(3-Cl)FAAY]-CO₂Me 
• 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 
• 1364705-55-4 Ac-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 
• 1364705-47-4 Boc-(cyclo-m,m)-[(3-Cl)FAY]-CO₂Me 
• 1364705-39-4 (S)-methyl 3-(4-(benzyloxy)-3-iodophenyl)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)propanoate 

Relevant academic research and scientific papers

Scalable Synthesis of Mycocyclosin

We report herein the scalable total synthesis of the secondary metabolite, mycocyclosin, initially isolated from Mycobacterium tuberculosis. Mycocylosin bears a highly strained 3,3′-dityrosine biaryl system which arises biosynthetically from an intramolec

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.

Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki reaction

(Matrix presented) 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-l