CAS: 9008-30-4; L-α-Lysophosphatidylcholine

该化合物是通过酶或化学水解,从磷酸酯中衍生出的生物活性磷素类,由附于甘油基脊的单一脂肪酸链组成,与磷胆碱头组相连;长效磷在细胞膜改造,信号转换和脂肪新陈代谢中发挥着关键作用;它们的非栖息性使其在药物运载系统中具有价值,提高了溶解性和对疏水化合物的生物利用性;在研究中,长效磷酸酯被用作脂肪合成的中间体和代谢紊乱的生物标志;它们在生物化学应用中的多功能,加上其结构特性,突出其在工业和学术环境中的重要性.

结构式图片

合成工艺路线路线简述

    📜乙酸乙烯酯,甘磷酸胆碱置于candida Antarctica Lipase体系中,用 水,叔丁醇 作为反应溶剂,化学反应 52.0H,反应生成 溶血卵磷脂(猪或牛肝)
    参考文献:液相色谱/质谱法合成和鉴定acedoxypc,一种含保护蛋白的结构化磷脂.
    标题:液相色谱/质谱法合成和鉴定acedoxypc,一种含保护蛋白的结构化磷脂.
    摘要:脂肪酸在从心血管疾病到脑疾病的多种疾病中具有许多健康益处.例如,二十二碳六烯酸(dha)富含脑磷脂,在抗炎或神经保护途径中起着重要作用.据认为,其作用部分归因于其转化为衍生的介体,如保护素.1-Lyso,2-二十二碳六烯酰基-甘油磷酸胆碱(lysoptdcho-Dha)是dha进入大脑的生理载体之一.我们以前合成的结构化磷脂酰胆碱,以模拟1-溶血,2-Docosahexaenoyl,甘油,命名acedopc ®(1-乙酰基,2-二十二碳六烯酰基-甘油磷酸胆碱),被认为是生理性lysoptdcho-Dha的稳定形式,在实验性缺血性中风中具有神经保护作用.考虑到这些,目前的研究旨在酶促氧合dha包含在acedopc ®合成含有保护素dx(pdx)易于构造氧化磷脂,此后命名acedoxypc(1-乙酰基,2-Pdx-甘油磷酸胆碱).使用液相色谱/串联质谱法鉴定该产物.这样的分子可用作用于抗神经退行性疾病和中风的治疗的生物活性介质.
    DOI:10.1007/s11745-017-4280-Z

    海关参考信息

    专利信息


    专利号:US-6451543-B1
    优先权日:1998-08-31
    标题:Lipid matrix-assisted chemical ligation and synthesis of membrane polypeptides
    发明人:KOCHENDOERFER GERD G; HUNTER CHRISTIE L; KENT STEPHEN B H; BOTTI PAOLO
    权利人:GRYPHON SCIENCES
    摘要:The present invention relates to methods and compositions for lipid matrix-assisted chemical ligation and synthesis of membrane polypeptides that are incorporated in a lipid matrix. The invention is exemplified in production of a prefolded membrane polypeptide embedded within a lipid matrix via stepwise chemoselective chemical ligation of unprotected peptide segments, where at least one peptide segment is embedded in a lipid matrix. Any chemoselective reaction chemistry amenable for ligation of unprotected peptide segments can be employed. Suitable lipid matrices include liposomes, micelles, cell membrane patches and optically isotropic cubic lipidic phase matrices. Prefolded synthetic and semi-synthetic membrane polypeptides synthesized according to the methods and compositions of the invention also permit site-specific incorporation of one or more detectable moieties, such as a chromophore, which can be conveniently introduced during synthesis. The methods and compositions of the invention have multiple uses. For example, they can be used to assay ligand binding to membrane polypeptides and domains comprising a receptor, and thus are extremely useful for structure/function studies, drug screening/selection/design, and diagnostics and the like, including high-throughput applications. The methods and compositions of the invention are particularly suited for FRET analyses of previously inaccessible membrane polypeptides.

    专利号:US-8314209-B2
    优先权日:2007-12-12
    标 题 :Lipid-assisted synthesis of polymer compounds and methods for their use
    发明人:RAJAMANI SUDHA; OLASAGASTI FELIX; DEAMER DAVID W; BENNER SEICO
    权利人:RAJAMANI SUDHA; OLASAGASTI FELIX; DEAMER DAVID W; BENNER SEICO; UNIV CALIFORNIA
    摘要:The invention herein disclosed provides for methods for the synthesis of polymers from monomers. In particular the method provides for the synthesis of polynucleotides from mononucleotides in the absence of catalytic enzymes. The method comprises providing an aqueous solution having a plurality of phospholipid molecules and monomer molecules; subjecting the aqueous solution to fluctuating temperature conditions; subjecting the aqueous solution to fluctuating cycles of drying and hydrating conditions; subjecting the aqueous solution to fluctuating [H + ] conditions; the fluctuating conditions thereby allowing formation of a chemical bond between at least two monomers to create a polymer. The invention is of particular use in the fields of molecular biology, structural biology, cell biology, molecular switches, molecular circuits, and molecular computational devices, and the manufacture thereof.

    专利号:US-6123959-A
    优先权日:1998-04-24
    标题:Aqueous composition comprising active ingredients for the de-pigmentation of the skin
    发明人:JONES KENNETH; PADMAPRIYA ABEYSINGHE; TEICHMUELLER ERNST E; BLUME GABRIELE
    权利人:UNIVERA PHARM INC; ROVI GMBH
    摘要:The present invention discloses aqueous compositions comprising liposomes of phospholipids, and at least one competitive inhibitor of an enzyme for the synthesis of melanin, in combination with at least one non-competitive inhibitor of an enzyme for the synthesis of melanin. The invention also includes the use of the compositions of this invention for the de-pigmentation of skin.

    专利号:US-8153615-B2
    优先权日:2005-06-10
    标 题:Synthesis of glycerolipid carbamates and dicarbamates and their use as an antitumor compounds
    发明人:BITTMAN ROBERT; BYUN HOE-SUP; ARTHUR GILBERT
    权利人:BITTMAN ROBERT; BYUN HOE-SUP; ARTHUR GILBERT
    摘要:The syntheses and in vitro antitumor properties of carbamate-containing, dicarbamate-containing, and ureido-containing phospholipid compounds that have an ether linkage at the C-1 position of a glycerol backbone, a carbamate, dicarbamate, or ureido moiety at the C-2 position of the glycerol backbone, and a phosphocholine, phosphonocholine, or glycoside moiety at the C-3 position of the glycerol backbone are described. The synthesis and antiproliferative activity of ether lipids with a naphthol moiety at the C-1 position are also described. These compounds were shown to be potent inhibitors of cancer cell growth. These compounds are useful for killing cancer cells and treating cancer.

    专利号:WO-9964032-A1
    优先权日:1998-06-08
    标题 :Combinatorial synthesis of multibinding libraries
    发明人:CHRISTENSEN BURTON G; GRIFFIN JOHN H; JENKINS THOMAS E; JUDICE J KEVIN
    权利人:ADVANCED MEDICINE INC; CHRISTENSEN BURTON G; GRIFFIN JOHN H; JENKINS THOMAS E; JUDICE J KEVIN
    摘要:Disclosed are methods for synthesizing large collections of diverse multimeric compounds as well as iterative processes for evaluating key molecular constraints imparting multibinding properties to multimeric compounds. Also disclosed are libraries of multimeric compounds which can be evaluated for imparting multibinding properties.

    专利号:US-9017974-B2
    优先权日:2011-06-06
    标题:Method for the synthesis of porphyrin-phospholipid conjugates
    发明人:ZHENG GANG; LOVELL JONATHAN
    权利人:ZHENG GANG; LOVELL JONATHAN; UNIV HEALTH NETWORK
    摘要:There is herein described a nanovesicle comprising a bilayer of porphyrin-phospholipid conjugates. Each porphyrin-phospholipid conjugate comprises one porphyrin, porphyrin derivative or porphyrin analog covalently attached to a lipid side chain at one of the sn-1 or the sn-2 positions of one phospholipid. Further, the nanovesicle has a defined regioisomeric ratio of sn-1:sn-2 porphyrin-phospholipid conjugates.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:A Practical Selective Synthesis Of Mixed Short/long Chains Glycerophosphocholines
    作者:Paola D'Arrigo,Ezio Fasoli,Giuseppe Pedrocchi-Fantoni,Cristina Rossi,Caterina Saraceno,Davide Tessaro,Stefano Servi |发布日期:2007.6
    摘要:1-Acyl-2-Lyso-Glycerophosphocholines. The Reaction Is Effective Using C-2 To C-16 Acid Chlorides In 2-Propanol. After Solvent Replacement The Lyso-Phospholipid (Lyso-Pl) Is Subjected To A Second Acylation Using Acid Anhydrides In Methylene Chloride. A Series Of 1(2)-Short-2(1)-Long-Diacyl-Glycerophosphocholines Are Obtained In High Yields And Selectivity. No Diacylation Product Was Detected. In Order To Detect

    合成参考文献


    参考文献:10.1016/j.jprot.2011.06.023
    摘要:Del Boccio P, Pieragostino D, Di Ioia M, Petrucci F, Lugaresi A, De Luca G, Gambi D, Onofrj M, Di Ilio C, Sacchetta P, Urbani A. Lipidomic investigations for the characterization of circulating serum lipids in multiple sclerosis. J Proteomics. 2011 Nov 18;74(12):2826–36. doi: 10.1016/j.jprot.2011.06.023.
    参考文献:10.1210/en.2005-0644
    摘要:Fujita Y, Yoshizumi M, Izawa Y, Ali N, Ohnishi H, Kanematsu Y, Ishizawa K, Tsuchiya K, Tamaki T. Transactivation of fetal liver kinase-1/kinase-insert domain-containing receptor by lysophosphatidylcholine induces vascular endothelial cell proliferation. Endocrinology. 2006 Mar;147(3):1377–85. doi: 10.1210/en.2005-0644.
    参考文献:10.3724/sp.j.1123.2011.00307
    摘要:Zhao S, Zheng H, Lu X, Liu Y, Su B, Xu G. [Metabonomics and phospholipid metabolic profiling of abnormal glucose metabolism based on high performance liquid chromatography-electrospray mass spectrometry]. Se Pu. 2011 Apr;29(4):307–13. doi: 10.3724/sp.j.1123.2011.00307.
    参考文献:10.3724/sp.j.1123.2011.00314
    摘要:Du Z, Zhang L, Liu S. [Application of liquid chromatography-mass spectrometry in the study of metabolic profiling of cirrhosis in different grades]. Se Pu. 2011 Apr;29(4):314–9. doi: 10.3724/sp.j.1123.2011.00314.
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