66076-38-8

Usage

Uses

Used in Pharmaceutical Industry:
N-T-BOC-PHE-TYR-DICYCLOHEXYLAMMONIUM is used as a coupling agent in peptide synthesis reactions for its ability to facilitate the formation of peptide bonds between amino acids. This enhances the efficiency and yield of peptide synthesis, which is vital for the development of new drugs and therapeutic agents.
Used in Research Applications:
In research settings, N-T-BOC-PHE-TYR-DICYCLOHEXYAMMONIUM is utilized as a key component in the synthesis of complex peptide sequences. Its stability and reactivity make it an indispensable tool for studying the structure, function, and interactions of peptides in various biological systems.

Upstream product

• 66076-54-8 N-tert-butyloxycarbonyl-L-phenylalanine-L-tyrosine methyl ester 
• 60-18-4 L-tyrosine 
• 514214-66-5 (S)-tert-butyl (1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 63-91-2 L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 50903-54-3 N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine pentafluorophenyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 3674-06-4 Boc-Phe-ONSu 
• 67729-36-6 Boc-Phe-O-COO-isoBu 

Downstream Products

• 906647-25-4 Boc-Phe-Tyr-Phe-OMe 
• 1621538-54-2 (S)-3-(4-{[((benzyloxy)carbonyl)-L-alanyl]oxy}phenyl)-2-{(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanamido}propanoic acid 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them

Prostate-specific membrane antigen (PSMA), also known as glutamate carboxypeptidase II (GCPII), is a suitable target for specific delivery of antitumor drugs and diagnostic agents due to its overexpression in prostate cancer cells. In the current work, we describe the design, synthesis, and biological evaluation of novel low-molecular PSMA ligands and conjugates with fluorescent dyes FAM-5, SulfoCy5, and SulfoCy7. In vitro evaluation of synthesized PSMA ligands on the activity of PSMA shows that the addition of aromatic amino acids into a linker structure leads to a significant increase in inhibition. The conjugates of the most potent ligand with FAM-5 as well as SulfoCy5 demonstrated high affinities to PSMA-expressing tumor cells in vitro. In vivo biodistribution in 22Rv1 xenografts in Balb/c nude mice of PSMA-SulfoCy5 and PSMA-SulfoCy7 conjugates with a novel PSMA ligand demonstrated good visualization of PSMA-expressing tumors. Also, the conjugate PSMA-SulfoCy7 demonstrated the absence of any explicit toxicity up to 87.9 mg/kg.

A Comprehensive Landscape for Fibril Association Behaviors Encoded Synergistically by Saccharides and Peptides

Nature provides us a panorama of fibrils with tremendous structural polymorphism from molecular building blocks to hierarchical association behaviors. Despite recent achievements in creating artificial systems with individual building blocks through self-

CONJUGATE OF FLUORESCENT DYE FOR THE VISUALIZATION OF PSMA EXPRESSING CELLS

The invention relates to the field of organic and medicinal chemistry, as well as molecular biology, and concerns a new class of compounds for imaging PSMA expressing cells and tissues, such as prostate cancer cells. New diagnostic conjugates for the visu

CONJUGATE MONOMETHYL AURISTATIN E TO OBTAIN A COMPOSITION FOR TREATMENT OF PROSTATE CANCER

?This invention is the conjugate of formula (I) for treatment of tumors expressing PSMA, including PSMA-ligand with linker and antineoplastic agent MMAE, the composition for lyophilizate preparation based on it, the dosage form for therapy and obtained by

Synthesis and photochemical reactivity of phthalimidoadamantane–tyrosine conjugates

Abstract: Dipeptide 3, tetrapeptide 4 and pentapeptide 5, containing adamantylphthalimide and tyrosine, were synthesized and their photochemical reactivity investigated. Upon excitation to the triplet excited state, 3 does not give any photoproduct, although the photoinduced electron transfer (PET) should take place based on the thermodynamic properties. Tetrapeptide 4 and pentapeptide 5 are photochemically reactive, undergoing decomposition upon excitation. The lack of anticipated photodecarboxylation reactivity is explained by PET between the tyrosine and the phthalimide. However, deprotonation of the phenoxyl radical-cation giving phenoxyl radicals or back electron transfer giving starting material are probably faster than intrastrand single electron transfer which would lead to carboxyl radical and decarboxylation. The results indicate the importance of fine-tuning the molecular structure to attain the desired photoreactivity by the right choice of the reactants redox potential, as well as their acid/base properties.

Photochemical formation of quinone methides from peptides containing modified tyrosine

We have demonstrated that quinone methide (QM) precursors can be introduced in the peptide structure and used as photoswitchable units for peptide modifications. QM precursor 1 was prepared from protected tyrosine in the Mannich reaction, and further used as a building block in peptide synthesis. Moreover, peptides containing tyrosine can be transformed into a photoactivable QM precursor by the Mannich reaction which can afford monosubstituted derivatives 2 or bis-substituted derivatives 3. Photochemical reactivity of modified tyrosine 1 and dipeptides 2 and 3 was studied by preparative irradiation in CH3OH where photodeamination and photomethanolysis occur. QM precursors incorporated in peptides undergo photomethanolysis with quantum efficiency ΦR = 0.1-0.2, wherein the peptide backbone does not affect their photochemical reactivity. QMs formed from dipeptides were detected by laser flash photolysis (λmax ≈ 400 nm, τ = 100 μs-20 ms) and their reactivity with nucleophiles was studied. Consequently, QM precursors derived from tyrosine can be a part of the peptide backbone which can be transformed into QMs upon electronic excitation, leading to the reactions of peptides with different reagents. This proof of principle showing the ability to photochemically trigger peptide modifications and interactions with other molecules can have numerous applications in organic synthesis, materials science, biology and medicine.

Solution-phase synthesis of chiral N-, O-, and S-acyl isopeptides

A convenient synthesis of chiral N-, O-, and S-acyl monoiso- and diisopeptides from di- and tripeptides containing tryptophan, tyrosine, and cysteine units using benzotriazole is reported in solution phase. Georg Thieme Verlag Stuttgart · New York.

α-N-Protected dipeptide acids: A simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide

The importance of dipeptides both in medicinal and pharmacological fields is well documented and many efforts have been made to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α-N-protected dipeptide acids by reacting the easily accessible mixed anhydride of α-N-protected amino acids with free amino acids under different reaction conditions. The combination of TBA-OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic solvents. Under these experimental conditions, the homogeneous phase condensation reaction occurs rapidly and without detectable epimerization. The present method is also applicable to side-chain unprotected Tyr, Trp, Glu, and Asp but not Lys. This latter residue is able to engage two molecules of mixed anhydride giving the corresponding isotripeptide. Moreover, the applicability of this protocol for the synthesis of tri- and tetrapeptides has been tested. This approach reduces the need for protecting groups, is cost effective, scalable, and yields dipeptide acids that can be used as building blocks in the synthesis of larger peptides.

Smart oligopeptide gels: In situ formation and stabilization of gold and silver nanoparticles within supramolecular organogel networks

Tripeptide with redox active chemical entities based smart organogels have been used for in situ formation and stabilization of gold and silver nanoparticles within the supramolecular gel networks and the gold nanoparticles are aligned in arrays along the gel nanofibers of peptide 1-toluene gels. The Royal Society of Chemistry 2006.