109-52-4Relevant academic research and scientific papers
A nickelacycle as propionic acid equivalent for carbon-carbon coupling reactions; application to the synthesis of C25 steroid carboxylic acids
Schonecker,Walther,Fischer,Nestler,Braunlich,Eibisch,Droescher
, p. 1257 - 1260 (1990)
β-Substituted propionic acids are prepared in good yields by carbon-carbon coupling reaction of the nickelacycle 1 with organic iodides and anhydrous manganese(II) iodide. This new reaction is used to the synthesis of C25 steroid carboxylic acids from C22 steroid iodides.
The plant pathogen enzyme AldC is a long-chain aliphatic aldehyde dehydrogenase
Lee, Soon Goo,Harline, Kate,Abar, Orchid,Akadri, Sakirat O.,Bastian, Alexander G.,Chen, Hui-Yuan S.,Duan, Michael,Focht, Caroline M.,Groziak, Amanda R.,Kao, Jesse,Kottapalli, Jagdeesh S.,Leong, Matthew C.,Lin, Joy J.,Liu, Regina,Luo, Joanna E.,Meyer, Christine M.,Mo, Albert F.,Pahng, Seong Ho,Penna, Vinay,Raciti, Chris D.,Srinath, Abhinav,Sudhakar, Shwetha,Tang, Joseph D.,Cox, Brian R.,Holland, Cynthia K.,Cascella, Barrie,Cruz, Wilhelm,McClerkin, Sheri A.,Kunkel, Barbara N.,Jez, Joseph M.
, p. 13914 - 13926 (2020)
Aldehyde dehydrogenases are versatile enzymes that serve a range of biochemical functions. Although traditionally considered metabolic housekeeping enzymes because of their ability to detoxify reactive aldehydes, like those generated from lipid peroxidation damage, the contributions of these enzymes to other biological processes are widespread. For example, the plant pathogen Pseudomonas syringae strain PtoDC3000 uses an indole-3-acetaldehyde dehydrogenase to synthesize the phytohormone indole-3-acetic acid to elude host responses. Here we investigate the biochemical function of AldC from PtoDC3000. Analysis of the substrate profile of AldC suggests that this enzyme functions as a long-chain aliphatic aldehyde dehydrogenase. The 2.5 ? resolution X-ray crystal of the AldC C291A mutant in a dead-end complex with octanal and NAD1 reveals an apolar binding site primed for aliphatic aldehyde substrate recognition. Functional characterization of site-directed mutants targeting the substrate- and NAD(H)-binding sites identifies key residues in the active site for ligand interactions, including those in the “aromatic box” that define the aldehyde-binding site. Overall, this study provides molecular insight for understanding the evolution of the prokaryotic aldehyde dehydrogenase superfamily and their diversity of function.
Synthesis of (E)-1-Aryl-1-alkenes via a Novel BF3·OEt2-Catalyzed Aldol-Grob Reaction Sequence
Kabalka, George W.,Li, Nan-Sheng,Tejedor, David,Malladi, Rama R.,Trotman, Sarah
, p. 3157 - 3161 (1999)
The reactions of aromatic aldehydes with ketones in the presence of various acids were examined. The reactions generate (E)-1-aryl-1-alkenes in the presence of boron trifluoride diethyl etherate in nonnucleophilic solvents.
Polyanhydride networks from thiol-ene polymerizations
Rutherglen, Broden G.,McBath, Ryan A.,Huang, Yu Ling,Shipp, Devon A.
, p. 10297 - 10303 (2010)
Thiol-ene photopolymerization was used in the synthesis of elastomeric polyanhydrides. Side reactions involving the addition of thiol to the anhydride were observed but take place at a much slower rate than photoinitiated thiol-ene polymerization. The thermomechanical properties, including the glass transition temperature (Tg) as well as tensile and compressive modulus, of the cross-linked material were studied using dynamic mechanical analysis. T g values ranged from -15 to approximately -50 °C and were dependent on the degree of cross-linking. The Young's and compressive modulus measurements confirm that these types of networks are a soft rubber-like material at room and body temperature and become softer as the cross-linking density is reduced. The hydrophobicity/hydrophilicity of these networks was analyzed by water contact angle measurements. The polyanhydrides were moderately hydrophobic, with water contact angle averages ranging from 82° to 92°. This hydrophobicity, coupled with the high reactivity of the anhydride groups, results in the material eroding via the surface erosion mechanism.
Oxidation of valeraldehyde by chlorine dioxide
Ganieva,Ganiev,Grabovskiy,Kabalnova
, p. 2332 - 2334 (2008)
The product of the reaction of valeraldehyde with chlorine dioxide was determined, and the solvent effect on the reaction kinetics was studied. The major oxidation product is valeric acid. The reaction rate is described by the second-order equation w = k[RCHO]?[ClO2]. The rate constants were measured in the 297-328 K interval, and the activation parameters of the reaction were determined.
A novel montmorillonite - KMnO4 system for the oxidation of alkenes under triphase conditions
Choudary,Valli,Prasad
, p. 2007 - 2013 (1991)
A very simple oxidation of alkenes to dicarboxylic acids using H-montmorillonite-KMnO4 system has been described for the first time.
Bi(III)-mandelate/DMSO : A New Oxidizing System for the Catalyzed C-C Cleavage of Epoxides
Zevaco, Thomas,Dunach, Elisabet,Postel, Michele
, p. 2601 - 2604 (1993)
Bi(III)-mandelate was found to be an effective catalyst for the oxidative C-C bond cleavage of epoxides and their transformation into carboxylic acids in anhydrous DMSO medium.
Controlling product selectivity by surface defects over MoOx-decorated Ni-based nanocatalysts for γ-valerolactone hydrogenolysis
Zhang, Guangcheng,Li, Wei,Fan, Guoli,Yang, Lan,Li, Feng
, p. 100 - 111 (2019)
Currently, highly efficient biomass upgrading over non-noble metal catalysts is of vital importance for reducing equipment and operation expenses in biorefinery industries. In this respect, the related heterogeneous catalysis demands the design and construction of mutual cooperative microstructure of catalysts to improve their catalytic performances. Here, an efficient catalytic process for selective hydrogenolysis of biomass-derived γ-valerolactone (GVL) to produce 1,4-pentanediol (1,4-PDO) and 2-methyltetrahydrofuran (2-MTHF) was developed by earth-abundant nickel-based catalysts, which were derived from a molybdate intercalated Ni-Al layered double hydroxide precursor. It was found that with the elevated reduction temperature, the amount of surface defective MoOx species (0 x/Al2O3 catalyst obtained at the reduction temperature of 600 °C delivered a 94.0% combined yield of 1,4-PDO and 2-MTHF under mild reaction conditions. It was demonstrated that over the present Ni-MoOx/Al2O3 catalyst system, surface defective MoOx species could greatly facilitate the adsorption and activation of carbonyl group in GVL and thus significantly promote the cleavage of C[dbnd]O bond and its adjacent C[sbnd]O bond. This finding opens a promising door to engineer surface defective structure of high-performance supported metal catalysts.
Catalytic Oxidation of Alcohol to Carboxylic Acid with a Hydrophobic Cobalt Catalyst in Hydrocarbon Solvent
Shi, Song,Liu, Meng,Zhao, Li,Wang, Min,Chen, Chen,Gao, Jin,Xu, Jie
, p. 2404 - 2409 (2017)
A hydrophobic cobalt catalyst was synthesized and proved to be effective in alcohol oxidation under the assistance of hydrocarbon solvent with oxygen as the terminal oxidant. A series of catalysts with different water contact angles was applied to investigate the hydrophobic effect. Further insight into the reaction process was gained by reaction kinetics, isotopic effect, etc. It showed that the hydrocarbon solvent participated in the alcohol oxidation, and with the aid of the in situ generated free radicals, the α-C?H bond was smoothly activated and the alcohol was converted to carbonyl compounds. The hydrophobic effect promoted the alcohol oxidation by affecting the solvent oxidation.
Two-Phase Flow Oxidation of Valeraldehyde with O2 in a Microstructured Reactor
Baumeister, Tobias,Kitzler, Hannes,Obermaier, Klemens,Zikeli, Stefan,R?der, Thorsten
, p. 1576 - 1579 (2015)
Microstructured reactors are the ideal device for highly exothermic reactions. In this work, the highly exothermic two-phase reaction of valeraldehyde with oxygen to valeric acid was carried out in a microreactor. The used device from one-A Engineering Austria GmbH is designed for process development and intensification and can be applied in the scale-up process to small-scale commercial production. The atom economic oxidation of valeraldehyde is performed at 0 to 40 °C with a catalytic amount of manganese(II) acetate. A continuous flow oxidation of aldehydes in such reactors can be a safe and beneficial alternative to commercial batch processes.
