65171-67-7

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 62-53-3 aniline 
• 107-59-5 tert-Butyl chloroacetate 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 6456-74-2 Glycine tert-butyl ester 
• 66003-78-9 triphenylsulfonium trifluoromethanesulfonate 
• 17763-67-6 Phenyl triflate 
• 35059-50-8 t-butyl diazoacetate 
• 108-86-1 bromobenzene 
• 27532-96-3 glycine tert-butyl ester hydrochloride 

Downstream Products

• 78773-98-5 N-(3-acetylthio-2-methylpropanoyl)-N-phenylglycine tert-butyl ester 
• 1240239-06-8 tert-butyl (S)-2-[N-phenyl-N-(1-phenyl-2-propynyl)amino]acetate 
• 1430654-33-3 C₂₀H₃₀N₂O₄ 
• 1430654-34-4 C₃₄H₄₈N₄O₆ 
• 1430654-28-6 C₁₈H₂₈N₂O₃ 
• 1430654-29-7 C₂₆H₃₅N₃O₄ 
• 1430654-30-0 C₃₂H₄₆N₄O₅ 
• 910810-27-4 ethyl 4-amino-1-phenyl-1H-pyrrole-3-carboxylate hydrochloride 
• 910810-30-9 ethyl 4-[(1-methylethyl)amino]-1-phenyl-1H-pyrrole-3-carboxylate hydrochloride 

Relevant academic research and scientific papers

Design, synthesis and evaluation of protein disulfide isomerase inhibitors with nitric oxide releasing activity

Protein disulfide isomerase (PDI), a chaperone protein mostly in endoplasmic reticulum, catalyzes disulfide bond breakage, formation, and rearrangement to promote protein folding. PDI is regarded as a new target for treatment of several disorders. Here, b

Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions

In this work, a visible-light-induced oxidative α-alkylation of glycine derivatives with ethers has been developed in the presence of catalytic Eosin Y. Under the blue light of a 3 W LED, a range of α-etherized glycine derivatives, including α-amino esters, α-amino ketones and α-amino amides, were achieved with good to excellent yields and functional group tolerance with tert-butyl hydroperoxide (TBHP) as oxidant at ambient temperature. The operationally easy procedure provides an economical, metal-free, and mild alternative for the synthesis of the α-etherized glycine derivatives.

Fluorescence Detection of Prostate Cancer by an Activatable Fluorescence Probe for PSMA Carboxypeptidase Activity

Prostate cancer (PCa) is a common malignant tumor among adult males, and convenient intraoperative detection of PCa would reduce the risk of leaving positive surgical margins, especially during nerve-sparing procedures. To achieve rapid, fluorescence-based visualization of PCa, we focused on the glutamate carboxypeptidase (CP) activity of prostate-specific membrane antigen (PSMA), a type II transmembrane glycoprotein that is attracting attention as a PCa biomarker. Based on our finding that aryl glutamate conjugates with an azoformyl linker are recognized by PSMA and have a sufficiently low LUMO (lowest unoccupied molecular orbital) energy level to quench the fluorophore through photoinduced electron transfer, we designed and synthesized a first-in-class activatable fluorescence probe for CP activity of PSMA. The developed probe allowed us to visualize the CP activity of PSMA in living cells and in clinical specimens from PCa patients and is expected to be useful for rapid intraoperative detection and diagnosis of PCa.

AMINOAMIDE COMPOUNDS

Compounds with amino amide linkers and pharmaceutical compositions and medicaments comprising such compounds are disclosed. The compounds modulate protein function of 1L-1β, IL-2, IL-6, TNF-α, CK1α, GSPT1, aiolos, ikaros or helios, or combinations thereof. In addition, methods of making such compounds and their uses for treating or ameliorating diseases, disorders, or conditions associated with protein malfunction, such as cancer, are provided.

Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates

A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.

Reagent-free continuous thermal tert-butyl ester deprotection

Continuous processing enables the use of non-standard reaction conditions such as high temperatures and pressures while in the liquid phase. This expands the chemist's toolbox and can enable previously unthinkable chemistry to proceed with ease. For a series of amphoteric amino acid derivatives, we have demonstrated the ability to hydrolyze the tert-butyl ester functionality in protic solvent systems. Using a continuous plug flow reactor at 120–240 °C and 15–40 min reaction times, no pH modification or additional reagents are needed to achieve the desired transformation. The method was then expanded to encompass a variety of more challenging substrates to test selectivity and racemization potential. The acid products were generally isolated as crystalline solids by simple solvent exchange after the deprotection reaction in good to high yield and purity.

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS

Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates

A general method for the N-arylation of amino acid esters with aryl triflates is described. Both α- and β-amino acid esters, including methyl, tert-butyl, and benzyl esters, are viable substrates. Reaction optimization was carried out by design of experim

Myoglobin-catalyzed intermolecular carbene N-H insertion with arylamine substrates

Engineered variants of the heme-containing protein myoglobin can efficiently catalyze the insertion of α-diazo esters into the N-H bond of arylamines, featuring a combination of high chemoselectivity, elevated turnover numbers, and broad substrate scope.

The tert-butyl side chain: A powerful means to lock peptoid amide bonds in the cis conformation

The very simple sterically hindered tert-butyl side chain exerts complete control over the peptoid amide geometry which only exists in the cis conformation. It is exemplified in NtBu glycine homo-oligomers and in linear oligopeptoids designed with an alte