- Synthesis and analysis of symmetrical and nonsymmetrical disaturated/monounsaturated triacylglycerols
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Symmetrical disaturated triacylglycerols of the structure SUS, where S is stearic acid (18:0) and U is an unsaturated fatty acid, either oleic (O; 9cis-18:1), linoleic (L; 9cis, 12cis-18:2), or linolenic (Ln; 9cis, 12cis, 15cis-18:3), are important components providing functionality to interesterified fat blends and structurally modified oils. Nonsymmetrical triacylglycerols of the structure SSU can significantly change melting point and solid fat content profiles. To characterize the physical properties of pure and symmetrical and nonsymmetrical triacylglycerol mixtures, the same reaction sequence has been used to prepare multigram quantities of triacylglycerols SUS and SSU. Tristearin was converted to a mixture of mono-, di-, and triacylglycerols, and the 1,3- and 1,2-diacylglycerol fraction was isolated by silica column chromatography. The 1,3-diacylglycerols were removed by crystallization from acetone and esterified with the appropriate fatty acid to form the symmetrical triacylglycerols with >99% SUS structure. The more difficult to obtain 1,2-diacylglycerols were prepared by esterification of the enriched 1,2-diacylglycerol fraction (80-86% 1,2-diacylglycerols) remaining after removal of much of the 1,3-isomer by crystallization, but silver resin or silver nitrate impregnated silica gel chromatography was required to isolate the nonsymmetrical triacylglycerols. SSL and SSLn were prepared in purities of >98% by this procedure, but not SSO. Silver ion HPLC was found to be as accurate as, and more rapid than, lipolysis/gas chromatography for the determination of the isomeric purities of the synthesized triacylglycerols.
- Adlof, Richard O.,List, Gary R.
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- Homogeneous Tubular-Flow Process for Monoolein Preparation
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Esterification of fatty acids with glycerol is characterized by negligible solubility of the two liquid phases. The reactions to mono-, di- and triglycerides taking place in the fatty acid phase, are limited by chemical equilibrium. The scope of this study is to investigate in a tubular reactor the conversion of a homogeneous mixture of oleic acid and glycerol in tert-butanol. The liquid composition in this study was 1 mol of oleic acid, 6 mol of glycerol and 14 mol of tert-butanol. Experiments were conducted in a tubular reactor at 35 atm over a temperature range of 200-240 °C and residence times of 0.7-17.6 h to determine the kinetics and the chemical equilibrium. The selectivity to monoolein was >95 mol %. A reversible second order reaction fits the data well.
- Herskowitz, Moti,Landau, Miron V.,Koukouliev, Slava,Zarchin, Ruby,Nehemya, Roxana Vidruk,Wee, Lik H.,Martens, Johan A.
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- Boronic acid-promoted site-selective Fischer esterifications of sugar alcohols
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A protocol for selective monoesterification of glycerol and pentose alcohols with fatty acids is described, using phenylboronic acid as a phase-transfer reagent. Formation of arylboronic ester intermediates serves both to increase the solubility of the alcohol substrate in nonpolar organic solvent and to selectively protect diol groups, allowing for efficient and selective condensation with the aliphatic carboxylic acid. A phase-switching workup with basic aqueous sorbitol solution is used to cleave the boronic ester groups and to separate the boronic acid from the monoester product. The method provides an operationally simple means of access to a class of bio-derived products that have been broadly applied as food additives, components of cosmetic products and pharmaceutical formations, plasticizers, and non-ionic surfactants.
- Manhas, Sanjay,Lin, Yu Chen,Wang, Grace,Kyne, Luke T.,Taylor, Mark S.
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Read Online
- Kinetic and docking study of synthesis of glyceryl monostearate by immobilized lipase in non-aqueous media
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Glyceryl monostearate is extensively used as an emulsifier in many industries. Mono acylation of glycerol was carried out by utilizing immobilized Candida antarctica lipase B (Cal B) as a biocatalyst and vinyl stearate as an acyl donor. Different reaction parameters, such as selection of lipases from various sources (like Candida antarctica, Candida rugosa, and Mucor meihei) and their quantity, shaking speed, temperature, substrate concentration, and reusability were studied in detail to achieve excellent conversion. Overall, 98% conversion of glycerol was obtained at a mole ratio of 1:1 of glycerol to vinyl stearate, using 12 mg of immobilized Cal B at 45 °C for 3 h. The mechanism of the given reaction was anticipated based on the results of the Lineweaver-Burk plots. It was found that the reaction followed the Ping-Pong Bi Bi mechanism with inhibition of glycerol. As it was a kinetically controlled synthesis, different kinetic constants were estimated by non-linear regression analysis. The activation energy for Cal B was found to be 10.3 kcal/mol. Further, biocatalyst can be reused up to four catalytic cycles with an average four percent loss of activity. A molecular docking study was done to find out the confirmation of substrates and their binding positions in an enzyme. It was noticed that the reaction proceeds through acyl-enzyme complex formation followed by the transfer of that acyl group to another substrate.
- Bhanage, Bhalchandra M.,Jawale, Priyanka V.
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- High-selectivity synthesis method of long-chain fatty acid monoglyceride
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The invention belongs to the field of fatty acid and synthetic fatty acid glycerides and relates to a high-selectivity synthesis method of long-chain fatty acid monoglyceride, in particular to a high-selectivity synthesis method of long-chain fatty acid and synthetic fatty acid glycerides. The method comprises the steps that tetraethyl silicate and glycerin are subjected to alcoholysis reaction, and part of glycerin is esterified to generate glyceryl silicate; then the glyceryl silicate is subjected to esterification reaction with fatty acid to generate fatty acid glyceride; finally the high activity (instability) of silicate ester is utilized to achieve hydrolysis under mild conditions to synthesize the synthetic fatty acid glyceride at high selectivity. A by-product is safe and harmlessSiO2. Accordingly, the product with high monoglyceride content is obtained by using a simple process under mild conditions.
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Paragraph 0035; 0038
(2019/02/27)
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- Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2
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The invention belongs to the field of fatty acid glyceride synthesis and nano powder preparation, relates to a method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2,and particularly relates to a method for synthesizing fatty acid monoglyceride and co-producing the nano SiO2 by long-chain fatty acid and glycerinum. The method comprises the following steps of: using silicon tetrachloride to react with the glycerinum, so as to enable the glycerinum to be partially esterified to generate silicic acid glyceride; and performing an esterification reaction with fatty acid to generate fatty acid silicic acid glyceride; finally using high-activity (instability) of silicate ester, hydrolyzing in a mild condition, synthesizing the high-content fatty acid monoglyceride, and by-producing SiO2 powder in a nano state. So that a fatty acid monoglyceride product is high-selectively obtained and nano SiO2 powder is co-produced by a simple technology in the mild condition.
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Paragraph 0039; 0042; 0043
(2019/03/28)
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- Method for synthesizing high content of fatty acid monoglyceride production of nano TiO2 The method of (by machine translation)
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The invention belongs to the fatty acid glyceride synthesis and nano powder preparation field. In particular to fatty acid and glycerin synthesis of fatty acid monoglyceride, and cogeneration nano TiO2 Method. Method of this invention is: for the reaction of titanium tetrachloride and glycerin, glycerol partial esterification, generating titanate glycerides. Then with the fatty acid esterification reaction, to generate fatty acid glyceride titanate. Finally the use of a titanate high activity (instability), hydrolysis under mild conditions, synthesizing high-content fatty acid monoglyceride, the pressure of the by-product TiO2 Powder. Thus a simple process, under mild conditions, a high content of fatty acid monoglyceride product, production of nano TiO2 Powder. (by machine translation)
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Paragraph 0039; 0042; 0043
(2019/03/28)
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- A glycerol monostearate synthesis method catalyzed by roasted hydrocalumite
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A glycerol monostearate synthesis method catalyzed by roasted hydrocalumite is disclosed. Glycerol monostearate is synthesized from methyl stearate and glycerol under the catalytic function of the roasted hydrocalumite. The hydrocalumite is synthesized from Ca(OH)2 and Al(OH)3 in a clean manner and is roasted to obtain a roasted hydrocalumite catalyst. The method has advantages of a low catalyst cost, a simple and clean preparation process, high product selectivity and easy separation of the catalyst from a product.
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Paragraph 0017; 0018; 0019; 0020; 0021
(2019/01/08)
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- Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids
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Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.
- Joshi, Alaumy,Shaikh, Minhaj,Singh, Shubham,Rajendran, Abinaya,Mhetre, Amol,Kamat, Siddhesh S.
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p. 16953 - 16963
(2018/11/21)
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- Lipidomics characterization of biosynthetic and remodeling pathways of cardiolipins in genetically and nutritionally manipulated yeast cells
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Cardioipins (CLs) are unique tetra-acylated phospholipids of mitochondria and define the bioenergetics and regulatory functions of these organelles. An unresolved paradox is the high uniformity of CL molecular species (tetra-linoleoyl-CL) in the heart, liver, and skeletal muscles-in contrast to their high diversification in the brain. Here, we combined liquid chromatography-mass-spectrometry-based phospholipidomics with genetic and nutritional manipulations to explore CLs' biosynthetic vs postsynthetic remodeling processes in S. cerevisiae yeast cells. By applying the differential phospholipidomics analysis, we evaluated the contribution of Cld1 (CL-specific phospholipase A) and Taz1 (acyl-transferase) as the major regulatory mechanisms of the remodeling process. We further established that nutritional "pressure" by high levels of free fatty acids triggered a massive synthesis of homoacylated molecular species in all classes of phospholipids, resulting in the preponderance of the respective homoacylated CLs. We found that changes in molecular speciation of CLs induced by exogenous C18-fatty acids (C18:1 and C18:2) in wild-type (wt) cells did not occur in any of the remodeling mutant cells, including cld1Δ, taz1Δ, and cld1Δtaz1Δ. Interestingly, molecular speciation of CLs in wt and double mutant cells cld1Δtaz1Δ was markedly different. Given that the bioenergetics functions are preserved in the double mutant, this suggests that the accumulated MLCL-rather than the changed CL speciation-are the likely major contributors to the mitochondrial dysfunction in taz1Δ mutant cells (also characteristic of Barth syndrome). Biochemical studies of Cld1 specificity and computer modeling confirmed the hydrolytic selectivity of the enzyme toward C16-CL substrates and the preservation of C18:1-containing CL species.
- Tyurina, Yulia Y.,Lou, Wenjia,Qu, Feng,Tyurin, Vladimir A.,Mohammadyani, Dariush,Liu, Jenney,Huttemann, Maik,Frasso, Michael A.,Wip, Peter,Bayir, Hulya,Greenberg, MiriaM. L.,Kagan, Valerian E.
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p. 265 - 281
(2018/01/02)
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- Glyceryl monostearate preparation method
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The invention belongs to the technical field of chemical synthesis, and relates to a glyceryl monostearate preparation method. Raw materials including stearic acid and glycerol carbonate are subjected to esterification reaction under the action of esterification catalysts and subjected to washing, reflux and chromatography to obtain intermediate products. The intermediate products and water are subjected to basic hydrolysis reaction under the action of hydrolysis catalysts and subjected to reflux, chromatography and decompression drying to obtain glyceryl monostearate. Compared with the prior art, the preparation method has the advantages that the purity of the obtained glyceryl monostearate can reach 93% or more, and the yield of the glyceryl monostearate can reach 90% or more under the condition of the preparation process superior to a traditional preparation process. Moreover, the production process is simple, the chemical principle is reliable, reaction conditions are mild, production equipment is simple, operation conditions are simple, product quality is good, the yield is high, investment cost is low, economic benefits are good, the whole production process is high in controllability, and industrial production is easily realized.
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Paragraph 0023; 0024; 0025; 0026; 0027; 0028; 0029-0042
(2017/06/29)
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- Preparation of glycerol monostearate from glycerol carbonate and stearic acid
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The chemical equilibrium for the preparation of glycerol monostearate (GMS) from glycerol carbonate (GC) and stearic acid (SA) was investigated. The chemical equilibrium constant K of the base-catalyzed synthesis of GMS from GC and SA was much smaller than that of the acid-catalyzed synthesis of (2-oxo-1,3-dioxolan-4-yl) methyl stearate (ODOMS) from GC and SA. In other words, it was thermodynamically difficult to obtain GMS with a high yield from GC and SA catalysed by basic catalysts. To prove this argument, we used magnesium oxide (MgO) as a catalyst to synthesize GMS from GC and SA. As expected, the yield of GMS was quite low. To increase the yield of GMS, a two-step procedure was proposed. First, pure ODOMS was synthesized by the esterification of GC with SA using copper p-toluenesulfonate (CPTS) as the catalyst. The conversion of SA reached 96.14% under the following conditions: reaction temperature, 140 °C; catalyst amount, 3% CPTS (based on the SA weight); reaction time, 3 h; GC-to-SA molar ratio, 1.5:1. Second, GMS was produced at a yield of 64.4% by the hydrolysis of ODOMS in the presence of triethylamine. The syntheses of ODOMS and GMS were confirmed by 1H- and 13C-NMR, FTIR and LC-MS analysis.
- Han, Li,Wang, Tao
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p. 34137 - 34145
(2016/05/19)
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- The chemical synthesis and preliminary biological studies of phosphodiester and phosphorothioate analogues of 2-methoxy-lysophosphatidylethanolamine
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The chemical synthesis of phosphorothioate/phosphodiester analogues of 2-methoxy-lysophosphatidylethanolamine has been described. For the preparation of phosphorothioate derivatives oxathiaphospholane approach has been employed. The phosphodiester compounds were prepared by OXONE oxidation of corresponding phosphorothioates. Each lysophospholipid analogue was synthesized as a series of four compounds, bearing different fatty acid residues both saturated (14:0, 16:0, 18:0) and unsaturated (18:1). The methylation of glycerol 2-hydroxyl function was applied in order to increase the stability of prepared analogues by preventing 1→2 acyl migration. The cytotoxicity of newly synthesized 2-methoxy-lysophosphatidylethanolamine derivatives was evaluated with resazurin-based method in prostate cancer PC3 cell line. The highest reduction of cell viability was noted for LPE analogues containing myristoyl acyl chain.
- Sowińska, Agata,Rytczak, Przemys?aw,Gendaszewska-Darmach, Edyta,Drzazga, Anna,Kozio?kiewicz, Maria,Okruszek, Andrzej
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p. 3725 - 3729
(2016/07/21)
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- Synthesis of glycerol monostearate over K2CO3/γ-Al2O3 catalyst
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The synthesis of glycerol monostearate by transesterification of methyl stearate with glycerol can be carried out in the presence of basic catalyst. The absence of solvent in the reaction system would result in a low conversion of methyl stearate as a consequence of low miscibility between reactants. The addition N,N′-dimethyl formamide as solvent improved the activity of the catalyst and selectivity to glycerol monostearate. Different K2CO3-containing γ-Al2O3 catalysts were made and used in the reaction. The results showed that catalyst with higher basicity could lead to better reactant's conversion but poorer selectivity to glycerol monostearate and the optimal load of K2CO3 inducing the highest yield to glycerol monostearate was 20 % mass fraction of γ-Al2O3 supporter. At a glycerol/methyl stearate ratio of 6:1, 165°C, 2 wt. % catalyst amount, a yield of 82.21 % of glycerol monostearate was achieved after 5h.
- Zhou, Lu,Gu, Yi,Hong, Mei,Xiao, Guomin
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p. 458 - 462
(2015/01/30)
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- Photopolymerizable Synthons from Glycerol Derivatives
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Photopolymerizable monomers based on monoglycerides were prepared by a convenient two-step procedure. The first one consists of the synthesis of highly pure monoglycerides by an organocatalyzed solvent-free route. This process was carried out by condensation of bio-sourced carboxylic acids (i.e. butyric, decanoic, undecylenic or stearic acids) with glycerol carbonate or glycidol in the presence of a quaternary ammonium salt as a catalyst. The obtained bio-based monoglycerides were modified in the second step by reaction with acryloyl and methacryloyl chloride leading to a series of new diacrylated and dimethacrylated monomers. The structures of the monoglycerides, diacrylated and dimethacrylated monomers were fully characterized by spectroscopic methods. Photopolymerization investigations monitored by infrared spectroscopy were achieved under ultraviolet radiation in the presence of a photoinitiator. The resulting cross-linked materials were analyzed by thermal gravimetric analysis, gel content determination and tests of swelling in water, ethanol and methylene chloride. Data relative to the pendulum hardness of these materials are also included.
- Mhanna, Ali,Sadaka, Faten,Boni, Gilles,Brachais, Claire-Helene,Brachais, Laurent,Couvercelle, Jean-Pierre,Plasseraud, Laurent,Lecamp, Laurence
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p. 337 - 348
(2014/03/21)
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- 1,2,3-Trimethoxypropane and glycerol ethers as bio-sourced solvents from glycerol: Synthesis by solvent-free phase-transfer catalysis and utilization as an alternative solvent in chemical transformations
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1,2,3-Trimethoxypropane (2), 1-alkoxy-2,3-dimethoxy-propanes, and 1-aryloxy-2,3-dimethoxypropanes were prepared in good yields and selectivity by solid-liquid phase-transfer catalysis in the presence of an inorganic base and an ammonium salt as the phase-transfer catalyst with no additional solvent. No heating was required, and the synthesis was easily performed under atmospheric pressure on a 150g scale. For the preparation of 2, the conversion of glycerol was complete and the selectivity for the expected glycerol trimethylether was above 95%. This product was utilized as a solvent in organic reactions such as transesterifications between glycerol and vegetable oil, organometallic reactions (Grignard- and Barbier-type reactions), carbon-carbon coupling reactions (Suzuki, Sonogashira, Heck), and in etherification reactions by dehydrogenative alkylation. The solvent showed interesting properties for the solubilization of polymers.
- Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
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p. 2893 - 2904
(2013/10/21)
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- 1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction
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From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.
- Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
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supporting information
p. 786 - 797
(2013/04/24)
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- The chemical synthesis and cytotoxicity of new sulfur analogues of 2-methoxy-lysophosphatidylcholine
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The chemical synthesis of phosphorothioate/phosphorodithioate analogues of 2-methoxy-lysophosphatidylcholine has been described. For the preparation of new sulfur derivatives of lysophosphatidylcholine both oxathiaphospholane and dithiaphospholane approaches have been employed. Each lysophospholipid analogue was synthesized as a series of five compounds, bearing different fatty acid residues both saturated (12:0, 14:0, 16:0, 18:0) and unsaturated (18:1). The methylation of glycerol 2-hydroxyl function was applied in order to increase the stability of prepared analogues by preventing 1→2 acyl migration. The cellular toxicity of newly synthesized 2-methoxy-lysophosphatidylcholine derivatives was measured using MTT viability assay and lactate dehydrogenase release method.
- Rytczak, Przemyslaw,Drzazga, Anna,Gendaszewska-Darmach, Edyta,Okruszek, Andrzej
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p. 6794 - 6798
(2014/01/06)
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- Pheromone synthesis. Part 253: Synthesis of the racemates and enantiomers of triglycerides of male Drosophila fruit flies with special emphasis on the preparation of enantiomerically pure 1-monoglycerides
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The racemates and enantiomers of triglycerides 1aee (2,3-ditigloyloxypropyl esters of palmitic, palmitoleic, stearic, oleic, and linoleic acids) of male Drosophila fruit flies were synthesized in three steps from the racemate and enantiomers of 2,3-acetoneglycerol (2) via 1-monoglycerides 4aee derived from the above fatty acids. Appropriate conditions were established for the preparation of enantiomerically pure 1-monoglycerides 4aee, and their enantiomeric purities were determined by NMR analysis of the corresponding bis-(R)-MTPA esters.
- Mori, Kenji
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p. 8441 - 8449
(2012/10/07)
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- 13C NMR quantification of mono and diacylglycerols obtained through the solvent-free lipase-catalyzed esterification of saturated fatty acids
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In the present investigation, we studied the enzymatic synthesis of monoacylglycerols (MAG) and diacylglycerols (DAG) via the esterification of saturated fatty acids (stearic, palmitic and an industrial residue containing 87% palmitic acid) and glycerol in a solvent-free system. Three immobilized lipases (Lipozyme RM IM, Lipozyme TL IM and Novozym 435) and different reaction conditions were evaluated. Under the optimal reaction conditions, esterifications catalyzed by Lipozyme RM IM resulted in a mixture of MAG and DAG at high conversion rates for all of the substrates. In addition, except for the reaction of industrial residue at atmospheric pressure, all of these products met the World Health Organization and European Union directives for acylglycerol mixtures for use in food applications. The products were quantified by 13C NMR, with the aid of an external reference signal which was generated from a sealed coaxial tube filled with acetonitrile-d3. After calibrating the area of this signal using the classical external reference method, the same coaxial tube was used repeatedly to quantify the reaction products. Copyright
- Fernandes, Jane Luiza Nogueira,De Souza, Rodrigo Octavio Mendonca Alves,De Vasconcellos Azeredo, Rodrigo Bagueira
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experimental part
p. 424 - 428
(2012/08/14)
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- The chemical synthesis of metabolically stabilized 2-OMe-LPA analogues and preliminary studies of their inhibitory activity toward autotaxin
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The chemical synthesis of five new metabolically stabilized 2-OMe-LPA analogues (1a-e) possessing different fatty acid residues has been performed by phosphorylation of corresponding 1-O-acyl-2-OMe-glycerols which were prepared by multistep process from racemic glycidol. The now analogues were subjected to biological characterization as autotaxin inhibitors using the FRET-based, synthetic ATX substrate FS-3. Among tested compounds 1-O-oleoyl-2-OMe-LPA (1e) appeared to be the most potent, showing ATX inhibitory activity similar to that of unmodified 1-O-oleoyl-LPA. Parallel testing showed, that similar trend was also observed for corresponding 1-O-acyl-2-OMe-phosphorothioates (2a-e, synthesized as described by us previously). 1-O-oleoyl-2-OMe-LPA (1e) was found to be resistant toward alkaline phosphatase as opposed to unmodified 1-O-oleoyl-LPA.
- Gendaszewska-Darmach, Edyta,Laska, Edyta,Rytczak, Przemys?aw,Okruszek, Andrzej
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supporting information; body text
p. 2698 - 2700
(2012/05/20)
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- Composition and method of preparing a tomato-based topical formulation for enhanced healing of burns, ultraviolet and radiation erythema
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The present invention is a topical treatment. which can be in the form of cream, ointment, spray or other topically administered composition, which is used to enhance healing of burns, ultraviolet and radiation erythema. The treatment not only reduces pain and inflammation, prevents blistering, and maintains flexibility of the skin, but also accelerates the normal healing process.
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- The chemical synthesis of phosphorothioate and phosphorodithioate analogues of lysophosphatidic acid (LPA) and cyclic phosphatidic acid (CPA)
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The chemical synthesis of new sulfur analogues of lysophospholipids has been described, including phosphorothioate/phosphorodithioate derivatives of lysophosphatidic acids (LPA) and phosphorothioate/phosphorodithioate derivatives of cyclic phosphatidic acids (cPA). For the preparation of LPA and cPA derivatives both oxathiaphospholane and dithiaphospholane approaches have been employed. Each lysophospholipid analogue has been synthesized as a series of five compounds, bearing five different fatty acid residues, both saturated (12:0, 14:0, 16:0, 18:0) and unsaturated (18:1), in the form of ammonium salts. The phosphorodithioate analogues of LPA were obtained as triethylammonium salts, however these were not stable and decomposed when transformed into the ammonium salt by ion exchange in aqueous methanol solution. The new sulfur analogues of LPA and cPA may share interesting biological properties of their parent compounds, and previously synthesized derivatives may behave as regulators of many metabolic processes and hopefully show new biological activity.
- Rytczak, Przemyslaw,Koziolkiewicz, Maria,Okruszek, Andrzej
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experimental part
p. 1008 - 1017
(2010/08/05)
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- Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite
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Glycerol-fatty acid esterification has been conducted with lipase from Penicillium camembertii lipase immobilized on epoxy SiO2-PVA in solvent-free media, with the major product being 1-monoglyceride, a useful food emulsifier. For a given set of initial conditions, the influence of reaction was measured in terms of product formation and selectivity using different fatty acids as acyl donors. Results were found to be relatively dependent of the chain length of the fatty acids, showing high specificity for both myristic and palmytic acids attaining final mixture that fulfills the requirements established by the World Health Organization to be used as food emulsifiers.
- Freitas, Larissa,Paula, Ariela V.,dos Santos, Julio C.,Zanin, Gisella M.,de Castro, Heizir F.
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experimental part
p. 87 - 90
(2010/10/19)
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- Stable emulsion and process for preparing the same
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The invention relates to a stable emulsion comprising (a) an oil; (b) water; (c) a surfactant; and (d) solid particulate material, wherein an emulsion comprising the oil, water, and the surfactant has a transitional phase inversion point, wherein the stable emulsion contains droplets having a d50 value of below 1 μm, and wherein the shelf life time of an emulsion comprising compounds (a) to (d) is longer than the shelf life time of emulsions containing only compounds (a) to (c).
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- Monoglycerides from the brown alga Sargassum sagamianum: Isolation, synthesis, and biological activity
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Polyunsaturated fatty acid-derived monoglycerides were characterized from the marine brown alga Sargassum sagamianum, collected from Jeju Island, Korea. A new compound of this structural class was isolated and determined to be 1-octadecatetraenoyl glycerol, by combined spectroscopic methods. Based on the structures and bioactivity of these compounds, a series of monoglycerides were synthesized using glycerol and various fatty acids. Several compounds exhibited moderate to significant inhibition of phospholipase A2 and cyclooxygenase-2.
- Chang, Hyeun Wook,Jang, Kyoung Hwa,Lee, Doohyun,Kang, Hee Ryong,Kim, Tae-Yoon,Lee, Bong Ho,Choi, Byoung Wook,Kim, Sanghee,Shin, Jongheon
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body text
p. 3589 - 3592
(2009/04/11)
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- Efficient synthesis of α-monoglycerides via solventless condensation of fatty acids with glycerol carbonate
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Highly pure α-monoglycerides (5a-e) were successfully prepared in high yields by the condensation of fatty acids such as lauric, myristic, palmitic, stearic and oleic (2a-e) with glycerol carbonate (4-hydroxymethyl-1,3- dioxolan-2-one) (1) in the presence
- Ghandi, Mehdi,Mostashari, Abdoljalil,Karegar, Mojgan,Barzegar, Mina
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p. 681 - 685
(2008/12/22)
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- HYDROLASES, NUCLEIC ACIDS ENCODING THEM AND MEHODS FOR MAKING AND USING THEM
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The invention provides hydrolases, polynucleotides encoding them, and methods of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides, e.g., enzymes, having a hydrolase activity, e.g., an esterase, acylase, lipase, phospholipase (e.g., phosphlipase A, B, C and D acitvity, patatin activity, lipid acyl hydrolase (LAH) activity) or protease activity, including thermostable and thermotolerant hydrolase activity, and polynucleotides encoding these enzyme, and making and using these polynucleotides and polypeptides. The hydrolase activities of the polypeptides and peptides of the invention include esterase activity, lipase activity (hydrolysis of lipids), acidolysis reactions (to replace an esterified fatty acid with a free fatty acid), transesterification reactions (exchange of fatty acids between triglycerides), ester synthesis, ester interchange reactions, phospholipase activity and protease activity (hydrolysis of peptide bonds). The polypeptides of the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts, including the manufacture of cosmetics and nutraceuticals. In another aspect, the polypeptides of the invention are used to synthesize enantiomerically pure chiral products.
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Page/Page column 226; 17/138
(2008/06/13)
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- Design of well balanced hydrophilic-lipophilic catalytic surfaces for the direct and selective monoesterification of various polyols
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The transesterification process is a well known reaction of organic chemistry. However, the monoesterification of unprotected polyols such as glycerol or sucrose is much more complex and the design of selective catalysts is becoming a huge challenge in order to avoid many protection and deprotection steps, harmful for the cost and the environmental impact of the resulting process. In this study, we showed that the control of the hydrophilic-lipophilic balance of heterogeneous catalysts is a crucial key in order to tune both the catalyst activity and the monoester selectivity. Indeed, whereas homogeneous guanidine led to low selectivity toward monoesters, its anchorage on a hydrophilic solid support such as silica allowed us to prepare two basic hybrid organic-inorganic materials able to selectively afford monoesters in high yield and in an environmentally-friendly process, at low temperature and starting from an equimolecular mixture of unprotected polyols and various fatty methyl esters. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2005.
- Kharchafi, Ghizlane,Jerome, Francois,Adam, Isabelle,Pouilloux, Yannick,Barrault, Joel
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p. 928 - 934
(2007/10/03)
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- Stereospecific and regioselective opening of an oxirane system. A new efficient entry to 1- or 3-monoacyl- and 1- or 3-monoalkyl-sn-glycerols
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Acyl or alkyl glycidols in the presence of trifluoroacetic anhydride (TFAA) and trifluoroacetate anions, undergo a regioselective and stereospecific opening of the oxirane system to produce the bis(trifluoroacetylated) derivatives, from which the corresponding 1(3)-monoacyl-sn-glycerols or 1(3)-monoalkyl-sn-glycerols can be obtained directly in high purity (>99%) and in quantitative yields.
- Stamatov, Stephan D.,Stawinski, Jacek
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p. 1601 - 1605
(2007/10/03)
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- Xanthen-9-ylidene protecting groups in glycerol chemistry
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The preparation of racemic, (S)- and (R)-1,2-O-(xanthen-9-ylidene)glycerol 17a, 20a and 23a and racemic, (S)and (R)-1,2-O-(2,7-dimethylxanthen-9-ylidene)glycerol 17b, 20b and 23b is reported. The racemic derivatives 17a and 17b are converted into their st
- Reese, Colin B.,Yan, Hongbin
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p. 1807 - 1815
(2007/10/03)
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- Encapsulation of microparticles in teardrop shaped polymer capsules of cellular size
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Microparticles such as propagules of eukaryotic biocontrol agents are encapsulated in cellular-scale polymer capsules that have a diameter similar to normal eukaryotic cells in a range of about 10 μm to about 400 μm. The microparticles are encapsulated by adding a hydrophobic dispersion medium such as a mixture of chloroform and hexane or a mixture of corn oil and n-hexadecane having a specific gravity of about 1 and containing an emulsifier such as lecithin to an aqueous suspension of the microparticles and a polymer matrix precursor such as alginate, agitating vigorously to form a stable emulsion of microscopic globules containing a microparticle, and adding the emulsion to an aqueous solution containing a polymerizing agent such as calcium chloride to polymerize and precipitate the globules to form microparticles encapsulated in polymer matrix capsules that may be of a teardrop shape having a length of 40-200% longer than the diameter. Precipitation of the globules is regulated by substantially matching the Specific Gravity of the hydrophobic dispersion medium and the aqueous suspension. The microparticle may be a viable propagule of a weed pathogenic fungus to provide a herbicidal composition.
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- Study of the effect of DATEM. 1. Influence of fatty acid chain length on rheology and baking
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To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.
- Koehler, Peter,Grosch, Werner
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p. 1863 - 1869
(2007/10/03)
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- Preparation of monoglycerides by guanidine-catalyzed processes
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Glycerolysis of methyl stearate and tristearin has been carried out in the presence of alkylguanidines - strong nonionic bases - as catalysts. When applied at 10 mol%, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,2,3-tricyclohexylguanidine, and 1,3-dicyclohexyl-2-n-octylguanidine give monoglycerides in more than 90% selectivity, in a maximum of 6 h reaction time.
- Guimaraes Aguiar, Leila M.,Vargas, Rogerio Matheus
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p. 755 - 756
(2007/10/03)
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- 1H-Nuclear magnetic resonance spectroscopic studies of saturated, acetylenic and ethylenic triacylglycerols
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The 1H-NMR spectroscopic properties of 15 synthetic homologous saturated triacylglycerols of type AAA and 16 mixed saturated triacylglycerols of type ABA and AAB have been studied. Triacylglycerols containing short-chain fatty acids (2:0-6:0) are readily identified. Triacylglycerols containing medium- and long-chain fatty acid components are not differentiated. From the analysis of 19 acetylenic triacylglycerols of type AAA, ABA and AAB (containing positional isomers of acetylenic fatty acids), it is only possible to characterize triacylglycerols with acyl groups containing the acetylenic bond at the Δ2-Δ5 position. 1H-NMR analysis could not confirm the positions (α- or β-acyl) of the acetylenic acids in mixed triacylglycerols. In the study of 22 ethylenic triacylglycerols of type AAA containing positional isomers of (Z)- or (E)-ethylenic acids, molecules containing an ethylenic bond in the Δ2 position of the acyl chains were readily characterized, as the ethylenic protons in the α- and β-acyl chains were fully resolved. Triacylglycerols containing an unsaturated center at the position were characterized by the shifts of the 2-H protons. The spectra of the remaining triacylglycerol molecules were very similar and the position of the ethylenic system could not be determined by this technique.
- Lie Ken Jie, Marcel S.F.,Lam
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p. 155 - 171
(2007/10/03)
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- A FACILE SYNTHESIS OF 1(3)-ACYLGLYCEROLS
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A facile route is described for the synthesis of 1(3)-acylglycerols for the first time through hydroxylation of allyl esters of fatty acids with the novel reagent cetyltrimethylammonium permanganate in a non-aqueous medium.
- Gangadhar, A.,Subbarao, R.,Lakshminarayana, G.
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p. 2505 - 2514
(2007/10/02)
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