39613-68-8

Upstream product

• 35356-70-8 Methyl 2-acetamidoacrylate 
• 146631-00-7 [4-(benzyloxy)phenyl]boronic acid 
• 34805-17-9 methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride 
• 108-24-7 acetic anhydride 
• 28047-05-4 (S)-N-acetyl-p-methoxyphenylalanine 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 57177-83-0 O-benzyltyrosine methyl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 73535-46-3 N-ac-(O-benzyl)tyrosine 
• 1398115-16-6 C₁₈H₂₀N₂O₄ 
• 2440-79-1 N-acetyl-L-tyrosine methyl ester 

Relevant academic research and scientific papers

Easy access to drug building-blocks through benzylic C-H functionalization of phenolic ethers by photoredox catalysis

A visible light-mediated photocatalyzed C-C-bond forming method for the benzylic C-H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy is reported. This method allows the mild, selective generation of benzyl radicals in phenolic complex molecules and drug-like compounds, providing new entries in synthetic and medicinal chemistry.

Design, synthesis and evaluation of novel metalloproteinase inhibitors based on l-tyrosine scaffold

A series of novel l-tyrosine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and histone deacetylase 8 (HDAC-8). The results showed that these l-tyrosine derivatives exhibited inhibitory profiles against MMP-2 and HDAC-8. The compounds 6h (IC50 = 0.013 ± 0.001 μM) and 6j (IC 50 = 0.017 ± 0.001 μM) were equal potent MMP-2 inhibitors to the positive control NNGH (IC50 = 0.014 ± 0.001 μM). As for HDAC-8 inhibition, some of the hydroxamate compounds, such as 6d (IC 50 = 3.6 ± 0.2 μM) and 6c (IC50 = 5.8 ± 0.5 μM), were equal potent to the positive control SAHA (IC50 = 1.6 ± 0.1 μM). Structure-activity relationships were also briefly discussed.

Synthesis of unnatural amino acid derivatives via palladium-catalyzed 1,4-addition of boronic acids

Aryl and alkenyl amino acid derivatives were synthesized by a palladium-catalyzed 1,4-addition of the corresponding boronic acids to 2-acetamidoacrylate.

Proline-rich proteins - Deriving a basis for residue-based selectivity in polyphenolic binding

1H NMR titration experiments have been used to establish that minimal proline-based models show enhanced binding selectivity towards phenol in CDCl3, relative to other similarly protected amino acid residues. Cooperative binding effects appear to play a role, with sarcosine models affording binding constants to phenol intermediate to those obtained from proline models and other amino acid models. The mechanism for binding, based on DFT calculations and the application of Hunter's molecular recognition toolbox model, cannot be solely attributed to hydrogen bond strength, and appears to be mediated through C-H-π bonds and the rotational freedom of the amide substrate. The Royal Society of Chemistry 2008.