220440-11-9

Upstream product

• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 220440-10-8 C₆₅H₁₀₃O₁₅N₅SiO 
• 74163-81-8 L-Tic-OH 
• 383910-50-7 Cbz-leucylpropyl-L-(3-carboxy-1,2,3,4-tetrahydroisoquinoline)-O-Boc-threonine 
• 220440-09-5 C₆₅H₁₀₅N₅O₁₅Si 
• 383910-49-4 Cbz-leucylpropyl-L-(3-carboxy-1,2,3,4-tetrahydroisoquinoline)-O-Boc-threonine-OSEM 
• 383910-51-8 C₇₁H₁₁₉N₅O₁₅Si₂ 
• 126587-57-3 (3S,4R,5S)-4-Amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid (1S,2S,3R)-4-(tert-butyl-dimethyl-silanyloxy)-1-isopropyl-2-methoxymethoxy-3-methyl-butyl ester 
• 383910-47-2 N-Cbz-L-3-carboxy-1,2,3,4-tetrahydroisoquinoline-O-Boc-threonine-OSEM 
• 383910-48-3 L-3-carboxy-1,2,3,4-tetrahydroisoquinoline-O-Boc-threonine-OSEM 
• 79261-58-8 (S)-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-benzyl ester 
• 116939-86-7 ((benzyloxy)carbonyl)-L-leucyl-L-proline 

Relevant academic research and scientific papers

Total syntheses of conformationally constrained didemnin B analogues. Replacements of N2O-dimethyltyrosine with L-1,2,3,4-tetrahydroisoquinoline and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline

The design and synthesis of two conformationally constrained analogues of didemnin B are described. The [N,O-Me2Tyr5]residue of didemnin B was replaced with L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline-3-carboxylic acid (MeO-Tic), which mimic the N,O-dimethylated tyrosine while constraining the conformation of the molecule. Preliminary results indicate that the conformation of the [N,O-Me2Tyr5]residue closely matches the conformation imposed by the Tic replacement.

Synthesis and biological activity of [Tic5] didemnin B

A didemnin B analog containing a Tic (1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid) as a comformationally restrained replacement for tyrosine has been synthesized and shown to have comparable potency as a protein biosynthesis inhibitor. Synthetic hig