- Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis
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The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.
- Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi
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p. 3115 - 3125
(2019/04/26)
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- Synthesis of: N-acyl amide natural products using a versatile adenylating biocatalyst
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Natural products are secondary metabolites produced by many different organisms such as bacteria, fungi and plants. These biologically active molecules have been widely exploited for clinical application. Here we investigate TamA, a key enzyme from the biosynthetic pathway of tambjamine YP1, an acylated bipyrrole that is produced by the marine microorganism Pseudoalteromonas tunicata. TamA is a didomain enzyme composed of a catalytic adenylation (ANL) and an acyl carrier protein (ACP) domain that together control the fatty acid chain length of the YP1. Here we show that the TamA ANL domain alone can be used to generate a range of acyl adenylates that can be captured by a number of amines thus leading to the production of a series of fatty N-acyl amides. We exploit this biocatalytic promiscuity to produce the recently discovered class of N-acyl histidine amide natural products from Legionella pneumophila.
- Marchetti, Piera M.,Richardson, Shona M.,Kariem, Noor M.,Campopiano, Dominic J.
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supporting information
p. 1192 - 1196
(2019/07/31)
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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention generally relates to compositions and methods for inducing an adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 115
(2018/05/24)
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- LIPID NANOPARTICLE FORMULATIONS
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Improved formulations of lipid nanoparticles are provided. Use of the lipid nanoparticles for delivery of a therapeutic agent and methods for their preparation are also provided.
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Page/Page column 142
(2018/05/24)
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- Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
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Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
- Ghosh, Santanu,Jana, Chandan K.
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p. 260 - 266
(2018/02/19)
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- NUCLEOSIDE-MODIFIED RNA FOR INDUCING AN ADAPTIVE IMMUNE RESPONSE
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The present invention relates to compositions and methods for inducing adaptive immune response in a subject. In certain embodiments, the present invention provides a composition comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof. For example, in certain embodiments, the composition comprises a vaccine comprising a nucleoside-modified nucleic acid molecule encoding an antigen, adjuvant, or a combination thereof.
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Page/Page column 143
(2016/11/17)
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- Method and apparatus for manufacturing carboxylic acid amide compound
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The present invention relates to a process and an apparatus for producing a carboxylic acid amide compound, and more particularly, to a process for producing a carboxylic acid amide compound which alternately performs a reaction process of a first manufacturing process that promotes the reaction between a first carboxylic acid and a first ammonia in the presence of a first catalyst and a reaction process of a second manufacturing process that promotes the reaction between a second carboxylic acid and a first ammonia in the presence of a second catalyst wherein each of them is progressed alternately between each preparation process so that the reaction between the carboxylic acid and the ammonia, which is intermittently carried out by the respective preparation processes, can be continuously performed, and moreover, the time required for the respective preparation processes is shortened, so that the carboxylic acid amide compound can be produced in a large amount in a short time.
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Paragraph 0059-0062; 0076
(2017/06/02)
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- NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
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Compounds are provided having the following structure: (I) or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.
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Page/Page column 71
(2016/05/02)
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- Electrospray ionization and collision induced dissociation mass spectrometry of primary fatty acid amides
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Primary fatty acid amides are a group of bioactive lipids that have been linked with a variety of biological processes such as sleep regulation and modulation of monoaminergic systems. As novel forms of these molecules continue to be discovered, more emphasis will be placed on selective, trace detection. Currently, there is no published experimental determination of collision induced dissociation of PFAMs. A select group of PFAM standards, 12 to 22 length carbon chains, were directly infused into an electrospray ionization source Quadrupole Time of Flight Mass Spectrometer. All standards were monitored in positive mode using the [M + H]+ peak. Mass Hunter Qualitative Analysis software was used to calculate empirical formulas of the product ions. All PFAMs showed losses of 14 m/z indicative of an acyl chain, while the monounsaturated group displayed neutral losses corresponding to H2O and NH3. The resulting spectra were used to propose fragmentation mechanisms. Isotopically labeled PFAMs were used to validate the proposed mechanisms. Patterns of saturated versus unsaturated standards were distinctive, allowing for simple differentiation. This determination will allow for fast, qualitative identification of PFAMs. Additionally, it will provide a method development tool for selection of unique product ions when analyzed in multiple reaction monitoring mode.
- Divito, Erin B.,Davic, Andrew P.,Johnson, Mitchell E.,Cascio, Michael
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experimental part
p. 2388 - 2394
(2012/07/27)
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- Lipase-catalyzed transformations using poly(ethylene glycol) as solvent
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Candida antarctica lipase catalyzes a number of elementary reactions like alcoholysis, ammoniolysis and aminolysis in poly(ethylene glycol) (PEG) media. Reaction rates were comparable to or better than those observed in conventional organic reaction media and ionic liquids. It is envisaged that PEGs could have added benefits for performing biotransformations with highly polar substrates, which are sparingly soluble in common organic solvents.
- Kidwai, Mazaahir,Poddar, Roona,Bhardwaj, Saurav
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experimental part
p. 113 - 118
(2011/12/15)
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- Amidation of esters assisted by Mg(OCH3)2 or CaCl2
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Magnesium methoxide (Mg(OCH3)2) and calcium chloride have been shown to facilitate the direct aminolysis of esters by ammonia to primary amides. Methyl, ethyl, isopropyl, and tert-butyl esters were converted to the corresponding carboxamides in good yields. Reactions have been run on a larger scale and without the safety liability inherent in the use of magnesium nitride (Mg3N2). Ammonium chloride and amine hydrochlorides have been used successfully in the place of ammonia with magnesium methoxide.
- Bundesmann, Mark W.,Coffey, Steven B.,Wright, Stephen W.
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experimental part
p. 3879 - 3882
(2010/08/19)
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- Magnesium nitride as a convenient source of ammonia: Preparation of primary amides
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(Chemical Equation Presented) The use of magnesium nitride (Mg 3N2) as a convenient source of ammonia has been explored for the direct transformation of esters to primary amides. Methyl, ethyl, isopropyl, and tert-butyl esters are converted to the corresponding carboxamides in good yields (75-99%).
- Veitch, Gemma E.,Bridgwood, Katy L.,Ley, Steven V.
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scheme or table
p. 3623 - 3625
(2009/05/07)
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- Synthetic libraries of tyrosine-derived bacterial metabolites
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The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters were synthesized in solution-phase.
- Georgiades, Savvas N.,Clardy, Jon
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supporting information; experimental part
p. 3117 - 3121
(2009/04/03)
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- Design, synthesis, antibacterial, and QSAR studies of myristic acid derivatives
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A series of esters and amides of myristic acid was synthesized and tested in vitro for antibacterial activity against Gram-positive and Gram-negative bacteria. All the compounds showed activity comparable to that of the standard drug, ciprofloxacin. The structural characteristics governing antibacterial activity of myristic acid derivatives was studied using QSAR methodology. The results showed that the antibacterial activity could be modeled using the topological descriptor, valence molecular connectivity index. The predictive ability of the models was cross-validated by construction of a test set. The low residual activity and high cross-validated r2 values ( rcv2 ) observed indicated the predictive ability of the developed QSAR models.
- Narasimhan, Balasubramanian,Mourya, Vishnukant,Dhake, Avinash
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p. 3023 - 3029
(2008/09/20)
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- Heterocyclic-substituted alkylamide acat inhibitors
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Pharmaceutically useful compounds having ACAT inhibitory activity of the formula wherein n is 0, 1, or 2, for X other than tetrazole and n = 2 then R2 = R3 = H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; x is a 5-membered heteromonocyclic group containing at least one to four heteroatoms selected from the group consisting of isothiazole, oxazole, thiazole, imidazole, furan, thiophene, pyrrole, tetrazole, 1,2,3-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-oxadiazole said heteromonocyclic group being unsubstituted or substituted at any available position along the ring,
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- 9(Z)-Octadecenamide and Fatty Amides by Bacillus megaterium (B-3437) Conversion of Oleic Acid
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9(Z)-Octadecenamide, hexadecenamide, tetradecenamide and tetradecanamide were produced by a novel bioconversion of oleic acid with Bacillus megaterium NRRL B-3437.Although chemical synthesis is more practical, the bioconversion to fatty amides (5-7percent of total recovered lipids) was unique for its requirement of both enzymatic catalysis and equimolar oleic acid / ammonium salt substrates.Purified octadecenamide was obtained by silica gel and high-pressure liquid chromatographic procedures and was characterized by gas chromatography, mass spectrometry, infrared and nuclear magnetic resonance.KEY WORDS: Bacillus megaterium (B-3437), bioconversion, fatty amides, hexadecenamide, 9(Z)-octadecenamide, oleic acid.
- Kaneshiro, T.,Vesonder, R. F.,Peterson, R. E.,Weisleder, D.,Bagby, M. O.
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p. 491 - 494
(2007/10/02)
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- Isoxazolyl-substituted alkyl amide ACAT inhibitors
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Pharmaceutically useful compounds having ACAT inhibitory activity of the formula STR1 wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R2 =R3 =H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.
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- Reaction of N-Nitroso- and N-Nitro-N-alkylamides with Amines
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Several N-nitroso- and N-nitrocarboxamides have been characterized by 1H and 13C NMR spectroscopy.These compounds react with ammonia and aliphatic amines to afford mainly carboxamides of general formula RCONH2, RCONHR', or RCONR'R''.N-Nitrosocarboxamides and aromatic amines give poor yields of RCONHAr; by contrast, N-nitrocarboxamides and aromatic amines lead to RCONHAr in good yields.The higher thermal stability of the N-nitroamides as compared to N-nitrosoamides is advantageous in this connection; nevertheless, the principal advantage of the NNO2 group appears to be that it activates the nucleophilic attack to the carbonyl of the amide function more than the NNO group, as has been demonstrated by competitive experiments.The reaction of N-nitroso- and N-nitro-N-methylsulfonamides with ammonia and diethylamine has been studied as well; whereas N-methyl-N-nitro-p-toluenesulfonamide reacts as N-nitrocarboxamides, transnitration is predominant with N-methyl-N-nitroso-p-toluenesulfonamide.
- Garcia, Jordi,Gonzalez, Javier,Segura, Ramon,Urpi, Felix,Vilarrasa, Jaume
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p. 3322 - 3327
(2007/10/02)
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