- NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN
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The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.
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Page/Page column 52; 53
(2018/08/12)
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- Sterols and Fatty Acids of the Harmful Dinoflagellate Cochlodinium polykrikoides
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Sterol and fatty acid compositions were determined for Cochlodinium polykrikoides, a toxic, bloom-forming dinoflagellate of global significance. The major sterols were dinosterol (40% of total sterols), dihydrodinosterol (32%), and the rare 4α-methyl Δ8(14) sterol, amphisterol (23%). A minor sterol, 4α-methylergost-24(28)-enol was also detected (5.0%). The fatty acids had a high proportion of PUFAs (47%), consisting mainly of EPA (20%) and the relatively uncommon octadecapentaenoic acid (18: 5, 22%). While unlikely to be responsible for toxicity to fish, these lipids may contribute to the deleterious effects of this alga to invertebrates.
- Giner, José-Luis,Ceballos, Harriette,Tang, Ying-Zhong,Gobler, Christopher J.
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p. 249 - 252
(2016/02/27)
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- Dissociation of proton-bound complexes reveals geometry and arrangement of double bonds in unsaturated lipids
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Double bond position and stereochemistry in unsaturated lipids can have profound impact on biological properties and activities but the assignment of these features by mass spectrometry is frequently challenging. Conventional techniques for lipid identification rely on collision-induced dissociation (CID) and are most often unable to differentiate between lipid isomers, particularly those involving double bond position and geometry (i.e., cis and trans). In this study, CID performed on proton-bound complexes of fatty acid methyl esters and iodoaniline (and related reagents) reveals unusual fragmentation patterns. CID products are shown to result from proton transfer and are associated with specific structures of the unsaturated lipids. Notably, CID of these complexes can not only distinguish cis- and trans-fatty acid methyl esters, but also differentiate conjugated double bond arrangements from non-conjugated analogs. Herein, the mechanisms underpinning this unique CID behavior are investigated by stable isotope labeling and are proposed to involve both carbene and free radical intermediates.
- Pham, Huong T.,Prendergast, Matthew B.,Dunstan, Christopher W.,Trevitt, Adam J.,Mitchell, Todd W.,Julian, Ryan R.,Blanksby, Stephen J.
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p. 170 - 177
(2015/10/20)
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- Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27
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The catalytic activity of CYP175A1 toward monooxygenation of saturated and monounsaturated fatty acids of various chain lengths (C16-C24) has been investigated to assess the enzymatic properties of this orphan thermostable cytochrome P450 enzyme. The resu
- Goyal, Sandeep,Banerjee, Shibdas,Mazumdar, Shyamalava
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p. 7880 - 7890
(2013/01/15)
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- Optimizing reaction conditions for the isomerization of fatty acids and fatty acid methyl esters to their branch chain products
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In order to improve the oxidative stability and cold flow properties of oleic acid or methyl oleate, branch chain isomerization was conducted using a beta zeolite catalyst. Reaction conditions of temperature (200-300 °C), pressure (0.1-3.0 MPa), and co-catalyst (0-2 wt%) were optimized based on branch chain conversion and the cloud point of the ester following the isomerization reaction of oleic acid or methyl oleate. Fourier transform infrared spectroscopy (FTIR) and Gas Chromatograph equipped with Mass Spectrometry (GC/MS) analyses were used to analyze and quantify the isomerization product samples, while the cloud point of each sample was tested. The lowest and therefore, best cloud point measured was -15.2 °C at conditions of 200 °C, 3 MPa, and 2% co-catalyst using methyl oleate as a starting material. The highest branch chain conversion achieved was 50% under conditions of 300 °C, 1.5 MPa and 0% co-catalyst using oleic acid as a starting material. The use of oleic acid and methyl oleate is based on whether it is optimal to carry out the skeletal isomerization before or after the esterification reaction. Performing the isomerization reaction on the ester was preferred over the fatty acid based on the trans isomerization and cloud point results. Reducing the unbranched trans isomers was desirable in obtaining a low cloud point. AOCS 2010.
- Reaume, Stephen J.,Ellis, Naoko
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experimental part
p. 661 - 671
(2012/01/31)
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- Efficient synthesis of unsaturated 1-monoacyl glycerols for in meso crystallization of membrane proteins
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A highly efficient synthesis of unsaturated 1-monoacyl glycerols was established to fulfill the pressing need for materials that form lipidic mesophases utilized in membrane protein crystallization. Georg Thieme Verlag Stuttgart.
- Fu, Yu,Weng, Yue,Hong, Wen-Xu,Zhang, Qinghai
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p. 809 - 812
(2011/06/21)
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- DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS
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Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.
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Page/Page column 18; 21-22; 29
(2008/12/07)
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- One-electron reduction of methanesulfonyl chloride. The fate of MeSO 2CI?- and MeSO2? intermediates in oxygenated solutions and their role in the cis-trans isomerization of mono-unsaturated fatty acids
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The one-electron reduction of methanesulfonyl chloride (MeSO2Cl) leads, in the first instance, to an electron adduct MeSO2Cl ?- which lives long enough for direct detection and decays into sulfonyl radicals MeSO2? and Cl-, with k = 1.5 × 106 s-1. Both, MeSO2Cl ?- and MeSO2? showed a similar absorption in the UV with λmax of 320 nm. In the presence of oxygen, MeSO 2Cl?- transfers an electron to O2 and establishes an equilibrium with superoxide. The rate constant for the forward reaction was measured to 4.1 × 109 M-1 s -1, while for the back reaction only an interval of 1.7 × 105 to 1.7 × 106 M-1 s-1 could be estimated, with a somewhat higher degree of confidence for the lower value. This corresponds to an equilibrium constant in the range of 2.4 × 10 3 to 2.4 × 104. With reference to E°(O 2/O2?-) = -155 mV, the redox potential of the sulfonyl chloride couple, E°(MeSO2Cl/MeSO2Cl ?-), thus results between being equal to -355 and -414 mV (vs NHE). MeSO2Cl?- reduces (besides O2) 4-nitroacetophenone. The underlying electron transfer took place with k = 1.5 × 109 M-1 s-1, corroborating an E° for the sulfonyl chloride couple significantly exceeding the above listed lower value. The MeSO2? radical added to oxygen with a rate constant of 1.1 × 109 M-1 s-1. Re-dissociation of O2 from MeSO2OO? occurred only very slowly, if at all, that is, with k ? 105 s-1. MeSO 2? radicals can act as the catalyst for the cis-trans isomerization of several Z- and E-mono-unsaturated fatty acid methyl esters in homogeneous solution. The effectiveness of the isomerization processes has been addressed, and in the presence of oxygen the isomerization is completely suppressed.
- Tamba, Maurizio,Dajka, Katalin,Ferreri, Carla,Asmus, Klaus-Dieter,Chatgilialoglu, Chryssostomos
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p. 8716 - 8723
(2008/02/13)
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- Synthesis of trans-vaccenic acid and cis-9-trans-11-conjugated linoleic acid
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The preparation of the monounsaturated fatty acid, trans-vaccenic acid 4 (TVA), using both Wittig and one-pot Julia-Kocieński olefination protocol, was achieved in good yield. Similarly a Wittig approach was employed for the stereoselective synthesis of cis-9-trans-11-conjugated linoleic acid 2 from trans-2-nonenal and (8-carboxyoctyl)triphenylphosphonium bromide 12.
- Duffy, Patricia E.,Quinn, Sonia M.,Roche, Helen M.,Evans, Paul
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p. 4838 - 4843
(2007/10/03)
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- The kinetics of thiyl radical-induced reactions of monounsaturated fatty acid esters
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The time-dependent isomerizations and thiol additions of several Z- and E-monounsaturated fatty acid methyl esters catalyzed by alkanethiyl radicals during γ-radiolysis of tert-butyl alcohol solutions are analyzed on the basis of the radiation chemical yield of radicals and established rate data. This provides room-temperature rate constants for the reversible thiyl addition. Within experimental errors, they do not depend on the double bond position in the alkyl chains. Particularly noteworthy is the very fast β-elimination of thiyl radicals from alkyl radicals which carry a second β-substituent. It is supported by additional evidence obtained with a radical clock methodology, and the large preference of fragmentation to the E-isomers is attributed to different barriers for the formation of the E- and Z-transition states from the equilibrium radical structure.
- Chatgilialoglu, Chryssostomos,Altieri, Alessio,Fischer, Hanns
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p. 12816 - 12823
(2007/10/03)
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- Synthesis and Characterisation of Selectively Fluorinated Steric Acids (Octadecanoic Acids) and Their Tristearins: The Effect of Introducing One and Two Fluorine Atoms Into a Hydrocarbon Chain
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The synthesis and physical properties of 2,2',2''- and 12,12',12''-trifluorotristearins 2 and 3 and 12,12,12',12',12'',12''-hexafluorotristearin 4 are described.NMR, X-ray powder diffraction, melting point and differential scanning calorimetry analyses of these compounds are reported and comparisons are drawn with tristearin 1.Analysis of Langmuir film isotherms of the stearic acids gave the average area occupied by each molecule in a condensed monolayer and was used as a method to probe disorder in the hydrocarbon chains.Of the compounds studied, 3 possesses the closest behaviour to tristearin.The incorporation of a CF2 group into the lipid chain in 4 imparts unique physical properties to the tristearin and a novel thermodynamically stable polymorphic form (β'') is observed.This is attributed to a conformational change in the hydrocarbon chain induced by the CF2 groups.Langmuir film analysis of the selectively fluorinated stearic acids (octadecanoic acids) 7 and 8 reinforce this conclusion.
- Dasaradhi, Lakkaraju,O'Hagan, David,Petty, Michael C.,Pearson, Christopher
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p. 221 - 226
(2007/10/02)
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- Synthesis of Z-11-octadecenal, the sex pheromone of the wax moth
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A new synthesis of Z-11-octadecenal, the sex pheromon of the wax moth Achroia grisella starting from the methyl 10-undecenoate is elaborated. - Key words: insect pheromone, stereoselective synthesis; Wittig reaction; hydroboration.
- Grigor'eva, N. Ya.,Tsiklauri, P. G.,Buevich, A. V.
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p. 1079 - 1080
(2007/10/02)
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- INSECT PHEROMONES AND THEIR ANALOGS III. SYNTHESIS OF THE SEX ATTRACTANTS OF SOME LEPIDOPTERA
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A new route to the synthesis of a number of attractants of Lepidoptera (Argyrotaenia velutinana, Mamestra configurata, and Lycorea ceres ceres) have been developed.These substances are acetates of enols with the cis configuration: tetradec-11-en-1-ol, hexadec-11-en-1-ol, and octadec-11-en-1-ol, respectively.The constants of the substances obtained agree completely with those given in the literature.The method is based on the coupling of the C3, C5, and C7 aldehydes with methyl 11-bromoundecanoate (I) by the Wittig reaction.To obtain compound (I) from methyl undeca-2E,5E,10-trienoate or methyl undeca-10-enoate we used hydroboration according to Brown followed by hydrogenation and bromination of the alcohol obtained.The advantage of this method is the use as starting materials of esters of unsaturated acids readily obtained by the homogeneous catalytic co-oligomerization of 1,3-dienes with acrylates.
- Dzhemilev, U. M.,Balezina, G. G.,Volkova, L. A.,Krivonogov, V. P.,Tolstikov, G. A.
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