49650-88-6Relevant academic research and scientific papers
The toluene o-xylene monooxygenase enzymatic activity for the biosynthesis of aromatic antioxidants
Donadio, Giuliana,Sarcinelli, Carmen,Pizzo, Elio,Notomista, Eugenio,Pezzella, Alessandro,Di Cristo, Carlo,De Lise, Federica,Di Donato, Alberto,Izzo, Viviana
, (2015/05/05)
Monocyclic phenols and catechols are important antioxidant compounds for the food and pharmaceutic industries; their production through biotransformation of low-added value starting compounds is of major biotechnological interest. The toluene o-xylene monooxygenase (ToMO) from Pseudomonas sp. OX1 is a bacterial multicomponent monooxygenase (BMM) that is able to hydroxylate a wide array of aromatic compounds and has already proven to be a versatile biochemical tool to produce mono- and dihydroxylated derivatives of aromatic compounds. The molecular determinants of its regioselectivity and substrate specificity have been thoroughly investigated, and a computational strategy has been developed which allows designing mutants able to hydroxylate non-natural substrates of this enzyme to obtain high-added value compounds of commercial interest. In this work, we have investigated the use of recombinant ToMO, expressed in cells of Escherichia coli strain JM109, for the biotransformation of non-natural substrates of this enzyme such as 2-phenoxyethanol, phthalan and 2-indanol to produce six hydroxylated derivatives. The hydroxylated products obtained were identified, isolated and their antioxidant potential was assessed both in vitro, using the DPPH assay, and on the rat cardiomyoblast cell line H9c2. Incubation of H9c2 cells with the hydroxylated compounds obtained from ToMO-catalyzed biotransformation induced a differential protective effect towards a mild oxidative stress induced by the presence of sodium arsenite. The results obtained confirm once again the versatility of the ToMO system for oxyfunctionalization reactions of biotechnological importance. Moreover, the hydroxylated derivatives obtained possess an interesting antioxidant potential that encourages the use of the enzyme for further functionalization reactions and their possible use as scaffolds to design novel bioactive molecules.
Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers
Liu, Yajun,Park, Se Kyung,Xiao, Yan,Chae, Junghyun
supporting information, p. 4747 - 4753 (2014/06/24)
A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is
Synthesis of 2,6-disubstituted benzylamine derivatives as reversible selective inhibitors of copper amine oxidases
Lucchesini, Francesco,Pocci, Marco,Alfei, Silvana,Bertini, Vincenzo,Buffoni, Franca
, p. 1558 - 1567 (2014/03/21)
In order to obtain substrate-like inhibitors of copper amine oxidases (CAOs), a class of enzymes involved in important cellular processes as well as in crosslinking of elastin and collagen and removal of biogenic primary amines, we synthesized a set of benzylamine derivatives properly substituted at positions 2 and 6 and studied their biological activity towards some members of CAOs. With benzylamines 6, 7, 8 containing linear alkoxy groups we obtained reversible inhibitors of benzylamine oxidase (BAO), very active and selective toward diamine oxidase (DAO), lysyl oxidase (LO) and monoamine oxidase B (MAO B) characterized by a certain toxicity consequent to the crossing of the brain barrier. Poorly toxic, up to very active, reversible inhibitors of BAO, very selective toward DAO, LO and MAO B, were obtained with benzylamines 10, 11, 12 containing hydrophilic ω-hydroxyalkoxy groups. With benzylamines 13, 14, 15, containing linear alkyl groups endowed with steric, but not conjugative effects for the absence of properly positioned oxygen atoms, we synthesized moderately active inhibitors of BAO reversible and selective toward DAO, LO and MAO B. The cross examination of the entire biological data brought us to the conclusion that the bioactive synthesized compounds most likely exert their physiological role of reversible inhibitors in consequence of the formation of a plurality of hydrogen bonds or hydrophobic non-covalent interactions with proper sites in the protein. Accordingly, the reported inhibitors may be considered as a set of research tools for general biological studies and the formation of enzyme complexes useful for X-ray structure determinations aimed at the design of more sophisticated inhibitors to always better modulate the protein activity without important side effects.
Fluorescence-on response via CB7 binding to viologen-dye pseudorotaxanes
Singh, Anuradha,Yip, Wai-Tak,Halterman, Ronald L.
supporting information; experimental part, p. 4046 - 4049 (2012/11/07)
Fluorescence-on sensors typically rely on disrupting photoinduced electron transfer quenching of the excited state through binding the electron donor. To provide a more general fluorescence-on signaling unit, a quencher-fluorophore dyad has been developed in which quenching by electron transfer to a tethered viologen acceptor can be disrupted through complexation of the viologen by cucurbit[7]uril (CB7). Dyads of benzyl viologen-rhodamine B or a BODIPY fluorophore gave upon CB7 complexation 14- and 30-fold fluorescence enhancement, respectively.
PYRROLE DERIVATIVE
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Page 92, (2010/02/06)
A novel pyrrole derivative represented by the following formula (1) and a salt thereof: wherein R1 means substituted alkenyl, etc.; R2 means substituted benzoyl, etc.; and R3 to R5 each means hydrogen, alkyl, halogeno, etc. The derivative and salt have antidiabetic activity.
Selective formylation of alcohols in the presence of phenols with chloral
Ram, Ram N,Meher, Nabin Kumar
, p. 2997 - 3001 (2007/10/03)
Primary and secondary alcohols were formylated selectively in the presence of phenols by stirring with chloral in acetone over anhydrous K2CO3 at ambient temperatures in high yields.
