- 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and preparation method thereof
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The invention provides 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine and a preparation method thereof. The preparation method comprises the following steps: S1, performing a nucleophilic substitution reaction on glyceryldipalmitate and POCl3 under the action of tetrahydrofuran and alkali, and purifying a reaction product after completion of the reaction to obtain an intermediate 1, wherein theintermediate 1 is (R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitic acid; S2, performing a nucleophilic substitution reaction on the intermediate 1 and N-Fmoc-ethanolamine under the action of tetrahydrofuran and alkali, and purifying a reaction product after completion of the reaction to obtain an intermediate 2, wherein the intermediate 2 is (R)-3-(((2-( fluorenylmethoxy carbonylamino)ethoxy)(hydroxy)phosphoryl)oxy)propane-1,2-dipalmitate; and S3, performing a nucleophilic substitution reaction on the intermediate 2 under the action of a solvent and alkali to obtain the 1,2-dipalmitoyl-SN-glycerol-3-phosphoethanolamine. According to the preparation method provided by the embodiment of the invention, a final product is relatively high in purity, and byproducts are few.
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Paragraph 0048; 0073-0085
(2019/10/23)
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- A diacyl phosphatidyl ethanolamine preparation method (by machine translation)
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The invention provides a diacyl phosphatidyl ethanolamine preparation method, comprises the following steps: (1) solvent and organic/inorganic alkali under the action of, the formula I compound and phosphorus reagent undergo the substitution reaction, formula a intermediate 1; (2) in the same reaction system, intermediate 1 of an organic/inorganic the presence of an alkali, with 2 - (N - [...] carbonyl amino) ethanol or N - Boc protection of the ethanolamine undergo the substitution reaction, formula b intermediate 2; (3) in the same reaction system, intermediate 2 under the action of the oxidizing agent in the oxidation reaction, the compound of formula II; (4) the formula II compound in the solvent, under the action of alkali, phospholipid base hydrolysis, formula III compound. The advantage of this invention is characterized in that: the invention only needs two-step synthesis of the target product can be obtained, and the method is easy to control conditions, after treatment is simple, less side reaction, high yield, consistent with the requirements of industrial production. (by machine translation)
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Paragraph 0101; 0102; 0103
(2018/11/22)
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- Chelating agents with lipophilic carriers
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Compounds useful for associating with nanoparticle or microparticle emulsions to obtain magnetic resonance images permit control of the relaxivity of the signal and readily associate with the particulate components.
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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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- Method of lowering the viscosity of mucus
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The use of phospholipids of the following formula to reduce the viscosity of mucus in a patient is described: STR1 wherein one of X, Y, or Z represent: STR2 in which each R represents hydrogen or methyl, and each of the other two of X, Y, or Z represents --CO--R1 in which R1 represents linear or branched C11-21 alkyl or C11-21 alkenyl, unsubstituted or substituted with one or more substituents selected from the group consisting of halo, C1-6 linear or branched alkoxy or cyano.
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- Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins
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The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes 1a and 1b) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.
- Alcaraz, Marie-Lyne,Peng, Ling,Klotz, Philippe,Goeldner, Maurice
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p. 192 - 201
(2007/10/03)
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- A General Method for the Synthesis of Glycerophospholipids and Their Analogues via H-Phosphonate Intermediates
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A general chemical method for the synthesis of glycerophospholipids and their analogues via H-phosphonate intermediates has been developed.It was found that 1,2-dipalmitoylglycero-3-H-phosphonate, prepared by the reaction of 1,2-dipalmitoylglycerol with PCl3/imidazole, reacts with various hydroxylic components (choline tosylate, N-(tert-butoxycarbonyl)ethanolamine, N-(tert-butoxycarbonyl)-L-serine) in the presence of condensing agents to produce in high yield the corresponding glycero-3-H-phosphonate diesters.These can be converted into natural phospholipids via oxidation with iodine or into thio or seleno analogues by using sulfur or selenium as oxidant, respectively.
- Lindh, Ingvar,Stawinski, Jacek
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p. 1338 - 1342
(2007/10/02)
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