10.1016/S0960-894X(03)00253-1
The research focuses on the design and synthesis of phosphotyrosine mimetics, which are of significant interest as potential therapeutic agents and research tools for selectively inhibiting protein tyrosine phosphatases (PTPases). These enzymes play a crucial role in regulating tyrosine phosphorylation and cellular function, and their inhibition could have therapeutic potential for diseases such as diabetes, cancer, and osteoporosis. The study involved the synthesis of phenylalanine derivatives, designed to mimic phosphorylated tyrosine or to act as irreversible active site inhibitors of PTPases. Key chemicals used in the synthesis process included Fmoc-l-Tyr-(3-NO2)-OH, CDI, MeOH, SnCl2, phosgene, TsCl, pyridine, SO2Cl2, and various other reagents and solvents. The synthesized compounds were then incorporated into a combinatorial library and screened for their ability to inhibit four phosphatases, showing moderate potency and selectivity, with the type 2d phosphotyrosine mimetic exhibiting the best activity. However, further analysis of enzymatic inhibition was not possible due to the termination of operations at Molecumetics.
10.1021/jo00139a027
The research explores various aspects of organic chemistry, focusing on the reactions of hemiacetal esters with acids and alcohols, the synthesis and configuration determination of (R)-(-)-1,1,2-triphenyl-3,3-dimethylbutane, and the nitrogen-15 NMR and photoelectron spectroscopy of substituted N-phenylaziridines. The first study investigates the formation of mixed acetals and the thermolysis of hemiacetal esters using NMR spectroscopy, aiming to understand reaction mechanisms and equilibrium states. The second study synthesizes (R)-(-)-1,1,2-triphenyl-3,3-dimethylbutane and examines the stereochemistry of reactions involving benzhydryllithium and α-phenylneopentyl chloride, concluding that the optical purity of starting materials significantly affects the final product's configuration. The third study measures the 15N chemical shifts of N-arylaziridines and correlates them with shifts in anilines and anisoles, revealing high resonance dependence and smaller-than-expected steric effects. Key chemicals used across these studies include hemiacetal ester, acetic acid, diphenylmethyllithium, α-phenylneopentyl chloride, thionyl chloride, phosgene, and various substituted N-phenylaziridines.
10.2174/157017809790443005
The study presents a new method for preparing N-tosyl-L-phenylalanine chloromethyl ketone (TPCK), an irreversible serine protease inhibitor, without using toxic and explosive diazomethane. L-Phenylalanine is first tosylated to form N-tosyl-L-phenylalanine, which is then converted into its 4-nitrophenyl ester using DCC and DMAP. This ester reacts with dimethylsulfoxonium methylide, generated from trimethylsulfoxonium iodide and potassium tert-butoxide, to form a sulfur ylide. The sulfur ylide is subsequently treated with lithium chloride and methanesulfonic acid to produce the chloroketone, TPCK. This method achieves an overall yield of 36% and avoids the use of hazardous diazomethane, providing a safer and practical synthesis route.
10.1055/s-1985-31216
The research aims to improve the yield and purity of isocyanide synthesis using phosphoryl chloride and disopropylamine. Traditionally, isocyanides are synthesized by dehydrating formamides, often using reagents like phosgene or diphosgene, which are highly toxic and costly. This study explores an alternative method using phosphoryl chloride combined with disopropylamine as a base. The researchers found that replacing the commonly used triethylamine with disopropylamine significantly enhances the yield and purity of isocyanides, often eliminating the need for chromatographic purification. The method is particularly effective for synthesizing ferrocenylalkyl isocyanides, where other methods fail or produce impurities. The study concludes that this new method is milder, more reproducible, and yields higher purity isocyanides compared to traditional methods, making it a valuable improvement in the field of isocyanide synthesis.
10.1021/ja9710971
The research focuses on the solid-phase synthesis of artificial β-sheets, which are compounds designed to mimic the structure and hydrogen-bonding patterns of protein β-sheets. These artificial β-sheets are of interest for their potential as drug candidates and as model systems for studying protein structure and stability. The research aims to synthesize and study these structures with the goal of understanding β-sheet formation and developing biologically active peptidomimetic compounds. The synthesis process involves constructing peptide strands on Merrifield resin, attaching di- or triurea templates, connecting upper peptide and peptidomimetic strands, and cleaving the resulting artificial β-sheets from the resin. Key chemicals used in the process include di- and triurea derivatives, peptide and peptidomimetic strands, tert-butoxycarbonyl (Boc)-leucine Merrifield resin, phosgene, trifluoroacetic acid (TFA), triethylamine (TEA), and various isocyanates. The conclusions of the research highlight the efficiency of the solid-phase syntheses, which allow for the rapid assembly of these complex molecules with good yields, making solid-phase synthesis the preferred method for preparing artificial β-sheets.
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