25518-33-6

Basic information

• Product Name: methyl (tert-butoxycarbonyl)-L-valyl-L-tyrosinate
• Synonyms: methyl (tert-butoxycarbonyl)-L-valyl-L-tyrosinate
• CAS NO: 25518-33-6
• Molecular Weight: 394.468
• Mol File: 25518-33-6.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl (tert-butoxycarbonyl)-L-valyl-L-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (tert-butoxycarbonyl)-L-valyl-L-tyrosinate(25518-33-6)
• EPA Substance Registry System: methyl (tert-butoxycarbonyl)-L-valyl-L-tyrosinate(25518-33-6)

Safety Data

• Hazardous Substances Data: 25518-33-6(Hazardous Substances Data)

Upstream product

• 65689-37-4 (S)-3-(4-Benzyloxy-phenyl)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-propionic acid methyl ester 
• 13734-41-3 t-Boc-L-valine 
• 1080-06-4 L-Tyr-OMe 
• 3417-91-2 L-tyrosine methyl ester HCl 

Downstream Products

• 54244-57-4 H-Val-Tyr-OMe*HCl 
• 54244-58-5 Valyl-tyrosine Methyl Ester 
• 437754-00-2 4-{4-[2-(2-amino-3-methyl-butyrylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-butyric acid 
• 75957-68-5 Boc-Asp(OBzl)-Val-Tyr-OMe 
• 131697-22-8 Boc-Gln-Tyr-Asp-Val-Tyr-OMe 
• 131697-23-9 Boc-Gln-Tyr-Asp-Val-Tyr-NHNH₂ 
• 131697-21-7 Boc-Gln-Tyr-Asp(OBzl)-Val-Tyr-OMe 
• 122299-19-8 H-Gln-Tyr-Asp-Val-Tyr-OMe*TFA 
• 84860-04-8 H-Val-Tyr-OMe 
• 1322510-63-3 methyl (L)-valyl-O-[(5S)-5-[(6-amino-9H-purin-9-yl)methyl]-2-oxido-1,4,2-dioxaphosphinan-2-yl]-(L)-tyrosinate 
• 1575822-61-5 Boc-Val-DOPA-OMe 
• 70935-40-9 N-Boc-Val-Tyr-Val-OMe 
• 77456-95-2 N^α-tert-butoxycarbonylvalyltyrosine 

Relevant articles and documents

Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation

Alzheime?s disease (AD) is the most prominent neurodegenerative disorder with high medical need. Protein-protein-interactions (PPI) interactions have a critical role in AD where β-amyloid structures (Aβ) build toxic oligomers. Design of disease modifying multi target directed ligand (MTDL) has been performed, which disable PPI on the one hand and on the other hand, act as procognitive antagonists at the histamine H3 receptor (H3R). The synthetized compounds are structurally based on peptidomimetic amino acid-like structures mainly as keto, diketo-, or acyl variations of a piperazine moiety connected to an H3R pharmacophore. Most of them showed low nanomolar affinities at H3R and some with promising affinity to Aβ-monomers. The structure–activity relationships (SAR) described offer new possibilities for MTDL with an optimized profile combining symptomatic and potential causal therapeutic approaches in AD.

Copper-Promoted O-Arylation of the Phenol Side Chain of Tyrosine Using Triarylbismuthines

A general method for the O-arylation of the side chain of tyrosine using triarylbismuth reagents is reported. The reaction is mediated by copper diacetate, operates at 50 °C under oxygen in dichloromethane in the presence of pyridine, shows excellent functional group compatibility, and retains the integrity of the stereogenic center. The protocol was used to arylate the tyrosine residue of dipeptides and tripeptides.

Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: Synthesis, stability, antiviral activity, and in vivo transport studies

Eight novel single amino acid (6-11) and dipeptide (12, 13) tyrosine P-O esters of cyclic cidofovir ((S)-cHPMPC, 4) and its cyclic adenine analogue ((S)-cHPMPA, 3) were synthesized and evaluated as prodrugs. In vitro IC 50 values for the prodrugs (50 0.3-35 μM); there was no cytoxicity with KB or HFF cells at ≤100 μM. The prodrugs exhibited a wide range of half-lives in rat intestinal homogenate at pH 6.5 (30-1732 min) with differences of 3-10× between phostonate diastereomers. The tyrosine alkylamide derivatives of 3 and 4 were the most stable. (l)-Tyr-NH-i-Bu cHPMPA (11) was converted in rat or mouse plasma solely to two active metabolites and had significantly enhanced oral bioavailability vs parent drug 1 in a mouse model (39% vs 5%).