54059-85-7Relevant academic research and scientific papers
Construction of a smart temperature-responsive GPx mimic based on the self-assembly of supra-amphiphiles
Zou, Huixin,Sun, Hongcheng,Wang, Liang,Zhao, Linlu,Li, Jiaxi,Dong, Zeyuan,Luo, Quan,Xu, Jiayun,Liu, Junqiu
, p. 1192 - 1199 (2016)
Glutathione peroxidase (GPx) is a major defense against hydroperoxides as a kind of seleno-enzyme that protects cells from oxidative damage. A supramolecular vesicle with controllable GPx activity and morphology has been successfully constructed by the self-assembly of supra-amphiphiles formed by host-guest recognition between cyclodextrin and adamantane derivatives. By introducing thermosensitive poly(N-isopropylacrylamide) (PNIPAM) scaffolds and the catalytic moiety selenium into adamantane and cyclodextrin, respectively, the complex of catalysis-functionalized cyclodextrin with thermosensitivity-functionalized adamantane directed the formation of a supramolecular vesicle which acted as a GPx mimic at 37 °C. The self-assembled nanoenzyme exhibited an obvious temperature responsive characteristic and high GPx-like catalytic activity promoting the reduction of hydrogen peroxide (H2O2) with glutathione (GSH) as the reducing substrate at 37 °C. However, the vesicle disassembled when the temperature decreased to 25 °C due to the transition of PNIPAM between the coil and the globule. Interestingly, the catalytic activity changed along with the transformation of morphologies. The vesicle structure self-assembled at 37 °C provided the favorable microenvironment for the enzymatic reaction, hence we successfully developed a temperature-responsive nanoenzyme model. Moreover, the catalytic activity of the thermosensitive GPx mimic exhibited excellent reversibility and typical saturation kinetics behaviour similar to a natural enzyme catalyst. It is assumed that the proposed GPx model not only has remarkable advantages such as easy functionalization and facile preparation but also provided a new way to develop intelligent responsive materials.
About the factors which govern the ring-opening of α-lactams with benzylamine: I. The relative stability of the α-lactam and the substituent on nitrogen
Lengyel, Istvan,Cesare, Victor,Chen, Sihao,Taldone, Tony
, p. 677 - 695 (2007/10/03)
Eight α-lactams (aziridinones) of varying stability, one of them previously unreported, were synthesized and reacted with benzylamine. Three of the α-lactams, 1-(1-adamantyl)-3,3-dimethylaziridinone (2j), 3,3-dimethyl1-triphenylmethylaziridinone (2m), and
The Conversion of Phenols to Primary and Secondary Aromatic Amines via a Smiles Rearrangement
Coutts, Ian G. C.,Southcott, Mark R.
, p. 767 - 771 (2007/10/02)
The conversion of phenols to 2-aryloxy-2-methylpropanamides (1) and the Smiles rearrangement of these to N-aryl-2-hydroxy-2-methyl propanamides are described; hydrolysis of the latter compounds yields anilines.The scope and limitations of reaction are discussed.Routes, some involving α-lactams, from phenols to N-substituted derivatives of (1) have been developed.Under the conditions of the Smiles rearrangement these secondary 2-methylpropanamides can form directly anilides, N-alkylanilines, or benzoxazinones.
Photochemical Elimination of Molecular Nitrogen from 3,5,5-Trialkyl-3,5-dihydro-4H-1,2,3-triazol-4-ones. Aziridinones, Iminooxiranes and Products
Quast, Helmut,Meichsner, Georg,Seiferling, Bernhard
, p. 225 - 230 (2007/10/02)
The dihydro-1,2,3-triazolones 6 lose molecular nitrogen on irradiation (λ >/= 300 nm).Aziridinones 7, 1:1 mixtures of ketones 10 and isocyanides 11, and small amounts of isocyanates 12 are formed in inert solvents and at temperatures between -90 and +20 deg C.In dimethylformamide as solvent, however, the oxazolidinone -14 arises almost quantitatively from 6c besides traces of acetone and tert-butyl isocyanide (11c).On irradiation in pure methanol, 6b-d produce the α-methoxyamides -17b-d as major product and less acetone and 11c than in inert solvents.In contrast, the presence of sodium methoxide gives rise to the formation from 6c of significant amounts of the α-aminoester -15 besides -17c as well as acetone and 11c.The photolysis of 6c in dimethylformamide and methanol, respectively, is compared to the reaction of 6c in the dark but under otherwise identical conditions.The results are interpreted in terms of the nitrogen-extrusion leading to the acyclic aziridinone isomers 16 which either cyclize to yield the aziridinones 7 and the unstable iminooxiranes 9 or react with dimethylformamide or methanol.
