3026-45-7Relevant articles and documents
A General Method for the Synthesis of Glycerophospholipids and Their Analogues via H-Phosphonate Intermediates
Lindh, Ingvar,Stawinski, Jacek
, p. 1338 - 1342 (1989)
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.
Novel lung intelligent drug release system
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Paragraph 0030; 0038-0039, (2020/09/04)
The invention discloses a novel lung intelligent drug release system which comprises a targeted structure and a polypeptide adaptor, wherein the targeted structure is multivalent long-chain fatty acylphospholipid capable of being subjected to specific identification by a lung epithelial cell surface receptor SP-A; the polypeptide adaptor is used for connecting a drug with the targeted structure and is a polypeptide chain which can be specially hydrolyzed by specific protease; and the specific protease is expressed a lot only when lung cells have pathological features. According to the invention, the long-chain fatty acyl phospholipid is used as a specifically identified group so as to mediate cells to generate endocytosis, macromolecules in nucleic acid drugs or polypeptide drugs, which are difficult to pass through cell membranes, can be transferred into cells, and polypeptide which can be hydrolyzed by the specific protease expressed a lot at lung lesion sites is combined and used as the adaptor, so that the novel drug release system can enter lung cells in a targeted mode and intelligently identify the lung lesion sites to release the drug.
A diacyl phosphatidyl ethanolamine preparation method (by machine translation)
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Paragraph 0101; 0102; 0103, (2018/11/22)
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)
A new approach to the stereospecific synthesis of phospholipids. The use of L-glyceric acid for the preparation of diacylglycerols, phosphatidylcholines, and related derivatives
Roodsari, Farzaneh S.,Wu, Dongpei,Pum, Gregory S.,Hajdu, Joseph
, p. 7727 - 7737 (2007/10/03)
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.
