- Synthesis of phosphatidylcholine: An improved method without using the cadmium chloride complex of sn-glycero-3-phosphocholine
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An improved safe method that does not contaminate the environment with cadmium chloride, a toxic heavy metal salt, was developed for the synthesis of phosphatidylcholine (PC). PC was synthesized from sn-glycero-3-phosphocholine (GPC) and fatty acid in one step under mild conditions without the use of cadmium chloride. GPC was prepared from egg yolk PC and adsorbed by kieselguhr in a Teflon vessel. The GPC on kieselguhr was acylated with fatty acid in the presence of two reagents, dicyclohexylcarbodiimide for synthesis of fatty acid anhydride and 4-dimethylaminopyridine as an acylating catalyst, at 30°C overnight. The PC thus produced was purified by silica gel column chromatography. The yield of dioleoyl PC was 90% based on the starting material, GPC.
- Ichihara, Ken'ichi,Iwasaki, Hitomi,Ueda, Kaori,Takizawa, Ryoko,Naito, Hideko,Tomosugi, Mitsuhiro
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- Preparation method of dioleoyl phosphatidylcholine
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The invention provides a method for artificially synthesizing dioleoyl phosphatidylcholine (DOPC), which comprises the following steps of: using glycerol phosphatidylcholine and oleic acid as raw materials to carry out a condensation reaction, pulping the obtained product, filtering, and recrystallizing to obtain high-purity dioleoyl phosphatidylcholine. The dioleoyl phosphatidylcholine (DOPC) prepared by the method disclosed by the invention can be used as a pharmaceutic adjuvant for various types of medicines such as injections, tablets, capsules and the like.
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Paragraph 0030-0046
(2020/08/07)
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- cis-trans Isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals
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Thiyl radicals reversibly attack the double bonds of methyl oleate and dioleoyl phosphatidyl choline (DOPC), thus producing methyl elaidate and the corresponding phospholipids containing trans-fatty acid residues in high yield. These processes are radical chain reactions with relatively long chain lengths. The rate constant for the β-elimination of a thiyl radical from the adduct radical has been estimated to be 6 x 106 s-1 at ambient temperature. The cis-trans isomerization of fatty acid residues in DOPC vesicles (multilamellar vesicles and large unilamellar vesicles made by the extrusion technique) by a thiyl radical, generated from biologically relevant thiols, has also been studied in detail. The presence of 0.2 mM oxygen does not influence the effectiveness of cis-trans isomerization in both homogeneous solution and lipid vesicles. This process, which does not cause lipid degradation but permanent modification of the membrane constituents, ultimately influences the barrier properties and functions of biological membranes.
- Chatgilialoglu, Chryssostomos,Ferreri, Carla,Ballestri, Marco,Mulazzani, Quinto G.,Landi, Laura
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p. 4593 - 4601
(2007/10/03)
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- A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives
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A new stereospecific synthesis of phospholipid derivatives of 1,2- diacyl-sn-glycerols is reported. The synthesis is based on (1) the use of L- glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2- dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal ω-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.
- Roodsari, Farzaneh S.,Wu, Dongpei,Pum, Gregory S.,Hajdu, Joseph
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p. 7727 - 7737
(2007/10/03)
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- The development of improved cationic lipids for gene transfer into cystic fibrosis airway epithelial cells
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In an effort to improve the efficiency of cationic lipid mediated gene transfer, over 90 novel cationic lipids of diverse structural types were synthesized and evaluated in vitro. Four cationic lipids derived from phospholipids were examined. The most promising cationic lipid formulations were tested in vivo by intranasal or transtracheal instillation into the lungs of BALB/c mice. The most active formulations gave CAT reporter gene expression levels which are greater than 500 fold over that which could be attained using free DNA alone. Certain cationic lipid formulations have been shown to facilitate substantial expression of the CFTR (cystic fibrosis transmembrane conductance regulator) gene in vitro as determined by the SPQ and Ussing Chamber assays.
- Harris,Marshall,Lee,Siegel,Mcneilly,Yew,Nietupski,Nichols,Cherry,Wan,Jiang,Lane,Rowe,Scheule,Smith,Cheng
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p. 289 - 292
(2007/10/03)
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- A Convenient Synthesis of Platelet-Activating Factors and Their Analogues from Chiral Epichlorohydrin
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Two platelet activating factors (PAF) were conveniently prepared from optically active epichlorohydrin via 5 steps in 15-16percent total yield.Four analogues containing oleoyl, propyl, p-trifluoromethylphenoxy, and N,N-dimethyldithiocarbamoyl groups were also prepared.
- Tsuboi, Sadao,Takeda, Shinji,Yamasaki, Yasuhisa,Sakai, Takashi,Utaka, Masanori,et al.
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p. 1417 - 1420
(2007/10/02)
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