109-52-4Relevant articles and documents
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Kipping
, p. 1145 (1935)
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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.
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.
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Hurd,Christ
, p. 141,144 (1936)
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Walling,Buckler
, p. 6032,6037 (1955)
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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.
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.
Karrer,Testa
, p. 1019,1021 (1949)
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Moles,P.J.,Reid,S.T.
, p. 2283 - 2286 (1976)
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Octane oxidation into carboxylic acids
Svetlakov,Nikitin,Nikolaeva
, p. 1230 - 1231 (2005)
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New norterpenoids and a sphingolipid from Carissa opaca
Parveen, Shehla,Saleem, Muhammad,Riaz, Naheed,Ashraf, Muhammad,Qurat-Ul-Ain,Nisar, Muhammad Farrukh,Jabbar, Abdul
, p. 222 - 231 (2016)
Chemical investigations on the aerial parts of Carissa opaca resulted in the isolation and characterization of two new nor-triterpenoids (compounds 1 and 2) and a new sphingolipid (compound 3) together with six known compounds. The structures of all the isolates were established using spectral data. All the isolated compounds showed DPPH radical scavenging and enzyme inhibitory activities against enzymes acetylcholinesterase, butyrylcholinesterase, and lipoxygenase.
Experimental and computational studies on substituent effects in reactions of peracid-aldehyde adducts
Lehtinen, Christel,Nevalainen, Vesa,Brunow, G?sta
, p. 9375 - 9382 (2000)
Liquid phase oxidation of six branched and four linear aldehydes by dioxygen and m-chloroperbenzoic acid was studied experimentally. 2-Substituted (α-branched) aldehydes reacted to give formates (via Bayer-Villiger mechanism) whereas the related linear saturated aldehydes were converted to the corresponding carboxylic acids. Formation of both these products can be rationalized via rearrangement reactions of peracid-aldehyde adducts 1. Computational studies employing DFT methods at the DNPP level with the Spartan program (v5.0) were carried out in order to understand properties of those adducts. Conformational properties of the adducts 1 were found to shed light on the differences observed in the reactions of linear and branched adducts. (C) 2000 Elsevier Science Ltd.
Enabling industrial biocatalytic processes by application of silicone-coated enzyme preparations
Nieguth,Eckstein,Wiemann,Thum,Ansorge-Schumacher
, p. 2522 - 2528 (2011)
Composite particles of the commercial lipase preparation NZ435 and silicone (silcoat-NZ435) have recently been described as promising biocatalysts for synthetic use. In this study, their actual potential for enhanced performance in industrial applications was evaluated, focusing on scenarios where carrier disintegration and catalyst leaching constitute key limitations. All three investigated model reactions, the syntheses of myristyl myristate, poly(ethylene glycol) 400-coconut fatty acid monoester and ethylene oxide and propylene oxide copolymer (EO/PO)-oleic acid diester, were considerably improved in terms of the maximal number of reaction cycles performed with the same batch of catalyst, and consequently in terms of the obtainable product amount. The total turnover numbers (TTN) increased by a factor up to 50, making the realization of this type of reactions in an industrial process more feasible. The utility of silcoat-NZ435 for stereoselective transformations was demonstrated with the enantioselective acylation of 1-phenylethanol with vinyl butyrate, in which full retention of the excellent stereoselectivity of native NZ435 was observed. Moreover, it was demonstrated for the first time that the methodology by which silcoat-catalysts are obtained can be successfully transferred to alternative carriers and enzymes (e.g., protease, esterase and laccase), opening a broad field for the implementation and advancement of biocatalysis in industrial processes. Copyright
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Pritzkow
, p. 1668,1675 (1954)
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Davidson,J.M.
, p. 126 - 127 (1966)
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Cahiez et al.
, p. 463,467, 468 (1975)
Efficient, Aerobic, Ruthenium-Catalyzed Oxidation of Alcohols into Aldehydes and Ketones
Marko, Istvan E.,Giles, Paul R.,Tsukazaki, Masao,Chelle-Regnaut, Isabelle,Urch, Christopher J.,Brown, Stephen M.
, p. 12661 - 12662 (1997)
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Improved procedure for ruthenium-catalyzed oxidative cleavage of alkenes with IG(OH)5
Shoair, Abdel Ghany F.,Mohamed, Ramadan H.
, p. 59 - 64 (2006)
Oxidative cleavage of alkenes to carboxylic acids catalyzed by cis-[RuCl2-(bipy)2]·2H2O in the presence of IO(OH)5 has been studied in a biphasic (CH3CN-CCl 4-H2O; 1:1:2 v/v) solvent system. Ruthenium tetraoxide seems to be the active catalyst species. Copyright Taylor & Francis LLC.
Molecular oxygen oxidative carbon-carbon bond cleavage of α-ketols catalysed by Bi(III) carboxylates
Le Boisselier, Veronique,Coin, Christine,Postel, Michele,Dunach, Elisabet
, p. 4991 - 4996 (1995)
Bi(III)-mandelate catalyses the oxidative carbon-carbon bond cleavage, by molecular oxygen, of a series of α-ketols into the corresponding carboxylic acids. The reaction is accelerated in the presence of DMSO.
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Bhattacharyya,Nandi
, p. 143,144 (1959)
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Sharkey,Mochel
, p. 3000,3004 (1959)
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Piacenti et al.
, p. 3653 (1968)
Reduction of Isopropylidene Acylmalonates, 5-Acylbarbituric Acids, and 3-Acyl-4-hydroxycoumarins to the Corresponding Alkyl Derivatives by Sodium Cyanoborohydride-Acetic Acid
Nutaitis, Charles F.,Schultz, Rose Ann,Obaza, Judy,Smith, Francis X.
, p. 4606 - 4608 (1980)
Isopropylidene acylmalonates, 5-acylbarbituric acids, and 3-acyl-4-hydroxycoumarins are readily reduced to the corresponding alkyl derivatives by sodium cyanoborohydride-acetic acid.The cyclic substrates are readily prepared by the acylation of isopropylidene malonate, barbituric acid (or its N,N'-dimethyl derivative), and 4-hydroxycoumarin, according to procedures developed by other workers.The reductions take place upon addition of a 2 mol equiv of sodium cyanoborohydride to a mixture of the acyl compound and acetic acid.This reductive transformation completes a synthetic method for the preparation of the alkyl derivatives starting from the parent compound.
Radical-mediated Carbonylation of Alkyl Iodides in Aqueous Media
Sugiura, Masaharu,Hagio, Hiroyuki,Kobayashi, Shu
, p. 898 - 899 (2003)
Radical-mediated single carbonylation of alkyl iodides furnishing carboxylic acids proceeded in water using phosphinic acid as a radical initiator in the presence of a surfactant (CTAB). On the other hand, formation of double carbonylation product (α-keto carboxylic acid) along with single carbonylation product was observed for the first time, when the reaction was carried out in aqueous ethanol without any surfactants.
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Powell,Murray,Baldwin
, p. 1153 (1933)
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Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process
Fu, Qiang,Liang, Fu-Shun,Lou, Da-Wei,Pan, Gao-Feng,Wang, Rui,Wu, Min,Xie, Kai-Jun
, p. 2020 - 2024 (2022/03/31)
A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.
Green, homogeneous oxidation of alcohols by dimeric copper(II) complexes
Maurya, Abhishek,Haldar, Chanchal
, p. 885 - 904 (2020/12/18)
Three pyrazole derivatives, 3,5-dimethyl-1H-pyrazole (DMPz) (I), 3-methyl-5-phenyl-1H-pyrazole (MPPz) (II), and 3,5-diphenyl-1H-pyrazole (DPPz) (III), were prepared via reacting semicarbazide hydrochloride with the acetylacetone, 1-phenylbutane-1,3-dione, and 1,3-diphenylpropane-1,3-dione, respectively. Complexes 1–3 were isolated by reacting CuCl2·2H2O with I–III, respectively, and characterized by CHNS elemental analyses, FT-IR, UV-Vis, 1H and 13C NMR, EPR spectra, and TGA/DTA. Molecular structures of the pyrazole derivatives I–III and copper(II) complexes 2 and 3 were studied through single-crystal XRD analysis to confirm their molecular structures. Overlapping of hyperfine splitting in the EPR spectra of the dimeric copper(II) complexes 1–3 indicates that both copper centers do not possess the same electronic environment in solution. The copper(II) complexes are dimeric in solid state as well as in solution and catalyze the oxidation of various primary and secondary alcohols selectively. Catalysts 1–3 show more than 92% product selectivity toward ketones during the oxidation of secondary alcohols. Surprisingly primary alcohols, which are relatively difficult to oxidize, produce carboxylic acid as a major product (48%–90% selectivity) irrespective of catalytic systems. The selectivity for carboxylic acid rises with decreasing the carbon chain length of the alcohols. An eco-friendly and affordable catalytic system for oxidation of alcohols is developed by the utilization of H2O2, a green oxidant, and water, a clean and greener solvent, which is a notable aspect of the study.
Zeolite-Tailored Active Site Proximity for the Efficient Production of Pentanoic Biofuels
Chen, Shaohua,Chen, Tiehong,Chu, Shengqi,Gu, Qingqing,He, Jiang,Liu, Yuanshuai,Luo, Wenhao,Wang, Aiqin,Weckhuysen, Bert M.,Wu, Zhijie,Yang, Bing,Zhang, Tao,Zhang, Yafeng
supporting information, p. 23713 - 23721 (2021/09/22)
Biofuel production can alleviate reliance on fossil resources and thus carbon dioxide emission. Hydrodeoxygenation (HDO) refers collectively to a series of important biorefinery processes to produce biofuels. Here, well-dispersed and ultra-small Ru metal nanoclusters (ca. 1 nm), confined within the micropores of zeolite Y, provide the required active site intimacy, which significantly boosts the chemoselectivity towards the production of pentanoic biofuels in the direct, one-pot HDO of neat ethyl levulinate. Crucial for improving catalyst stability is the addition of La, which upholds the confined proximity by preventing zeolite lattice deconstruction during catalysis. We have established and extended an understanding of the “intimacy criterion” in catalytic biomass valorization. These findings bring new understanding of HDO reactions over confined proximity sites, leading to potential application for pentanoic biofuels in biomass conversion.
