CAS: 923-61-5; (2R)-3-(((2-Aminoethoxy)(Hydroxy)Phosphoryl)Oxy)Propane-1,2-Diyl Dipalmitate

该化合物是生物化学和细胞生物学中常用的磷素,其特点是两条棕榈酸链,饱和脂肪酸,造成其疏水性能;分子具有甘油基脊柱特征,在第一和第二位置被浸泡到两个脂肪酸链中,第三个位置与乙醇胺磷有关;这种结构具有闪烁特性,使DPPE能够在水中形成双层和卵囊,使其在乳腺研究和药物运载系统中必不可少;DPPE经常用于脂质配方,并用作各种应用的脂质双层的组成部分,包括薄膜动态和蛋白相互作用研究;它与生物系统的稳定性和兼容性使其成为研究和制药发展的宝贵工具;此外,DPPE可以参与各种生物化学反应,包括涉及膜聚和细胞信号路径的反应.

结构式图片

相似化合物

998-07-2 1069-79-0 4004-05-1

上下游产品

CAS号59540-20-4 2-(1',2'-dipalm... | CAS号57818-60-7 hexadecanoic ac... | CAS号30334-71-5 1,2-双棕榈酸甘油酯

合成工艺路线路线简述

  • 合成目标产物 1,2-Dipalmitoyl-Sn-Glycero-3-Phosphoethanolamine 主要起始原料 Hexadecanoic Acid, (1R)-1-[[[[bis(1-Methylethyl)Amino]Methoxyphosphino]Oxy]Methyl]-1,2-Ethanediyl Ester (9CI)
  • 1242411-29-5 = 923-61-5
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium
    标题:Antibacterial Effect Of Indene On Helicobacter Pylori Correlates With Specific Interaction Between Its Compound And Dimyristoyl-Phosphatidylethanolamine
    作者:Wanibuchi,Kiyofumi; Et Al
    参考文献:Chemistry And Physics Of Lipids 日期:2020 卷标:227]

    86030-43-5 + 24070-16-4 = 923-61-5
    反应条件:1.1 Reagents: Triethylamine Solvents: Chloroform1.2 Reagents: 1H-Tetrazole1.3 Solvents: Acetonitrile,Tetrahydrofuran1.4 Reagents: Tert-Butyl Hydroperoxide Solvents: Toluene2.1 Reagents: Trimethylamine Solvents: Toluene2.2 Reagents: Acetic Acid,Zinc
    标题:A General Method For The Synthesis Of Glycerophospholipids
    作者:Bruzik,Karol S.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1986 卷标:51(12) 页码:2368-70]

    59540-20-4 = 923-61-5
    反应条件:1.1 Reagents: Sodium Azide Solvents: Acetonitrile2.1 Reagents: Hydrogen Catalysts: Palladium
    标题:Antibacterial Effect Of Indene On Helicobacter Pylori Correlates With Specific Interaction Between Its Compound And Dimyristoyl-Phosphatidylethanolamine
    作者:Wanibuchi,Kiyofumi; Et Al
    参考文献:Chemistry And Physics Of Lipids 日期:2020 卷标:227]

    102152-58-9 = 923-61-5
    反应条件:1.1 Reagents: Trimethylamine Solvents: Toluene1.2 Reagents: Acetic Acid,Zinc
    标题:A General Method For The Synthesis Of Glycerophospholipids
    作者:Bruzik,Karol S.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1986 卷标:51(12) 页码:2368-70]

    119184-85-9 = 923-61-5
    反应条件:1.1 Reagents: Iodine Solvents: Pyridine,Water1.2 Reagents: Trifluoroacetic Acid,Perchloric Acid Solvents: Dichloromethane
    标题:A General Method For The Synthesis Of Glycerophospholipids And Their Analogs Via H-Phosphonate Intermediates
    作者:Lindh,Ingvar; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(6) 页码:1338-42]

    = 923-61-5 [标题:Reaction Conditions
    标题:Efficient Delivery Of Antitumor Drug To The Nuclei Of Tumor Cells By Amphiphilic Biodegradable Poly(L-Aspartic Acid-Co-Lactic Acid)/dppe Co-Polymer Nanoparticles
    作者:Han,Siyuan; Et Al
    参考文献:Small 日期:2012 卷标:8(10) 页码:1596-1606]

    26690-80-2 + 119184-81-5 = 923-61-5
    反应条件:1.1 Reagents: Pivaloyl Chloride Solvents: Pyridine2.1 Reagents: Iodine Solvents: Pyridine,Water2.2 Reagents: Trifluoroacetic Acid,Perchloric Acid Solvents: Dichloromethane
    标题:A General Method For The Synthesis Of Glycerophospholipids And Their Analogs Via H-Phosphonate Intermediates
    作者:Lindh,Ingvar; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1989 卷标:54(6) 页码:1338-42
(R)-3-(((2-(Fluorenylmethoxycarbonylamino)Ethoxy)(Hydroxy)Phosphoryl)Oxy)Propane-1,2-Dipalmitate置于1,8-二氮杂双环[5.4.0]十一碳-7-烯体系中,用 二氯甲烷 作为反应溶剂,化学反应 2.0H,以78%的收率获得产物l-磷脂酰乙醇胺
参考文献:1,2-二棕榈酰-Sn-甘油-3-磷酰乙醇胺及其制备方法
标题:1,2-二棕榈酰-Sn-甘油-3-磷酰乙醇胺及其制备方法
摘要:本发明提供一种1,2‑二棕榈酰‑sn‑甘油‑3‑磷酰乙醇胺及其制备方法,其中制备方法包括如下步骤:步骤s1,二棕榈酸甘油酯在四氢呋喃和碱的作用下,与pocl3发生亲核取代反应,在反应完成后对反应产物进行纯化,得到中间体1,所述中间体1为(R)‑3‑((二氯磷酰基)氧基)丙烷‑1,2‑二棕榈酸;步骤s2,所述中间体1在四氢呋喃和碱的作用下,与n‑fmoc‑乙醇胺发生亲核取代反应,在反应完成后对反应产物进行纯化,得到中间体2,所述中间体2为(R)‑3‑(((2‑(芴甲氧羰氨基)乙氧基)(羟基)磷酰基)氧基)丙烷‑1,2‑二棕榈酸酯;步骤s3,所述中间体2在溶剂和碱作用下,发生亲核取代反应,得到所述1,2‑二棕榈酰‑sn‑甘油‑3‑磷酰乙醇胺.根据本发明实施例的制备方法,最终产物纯度较高,副产物少.

海关参考信息

专利信息


专利号:US-2024294462-A1
优先权日:2023-02-15
标题:Method for the Synthesis of Ionizable Lipids Using a Doubly Alkylated Intermediate
发明人:SAADATI FARIBA; TRAN HUY; CIUFOLINI MARCO; ATMURI N D PRASAD
权利人:NANOVATION THERAPEUTICS INC
摘要:Provided herein is a method for the preparation of ionizable, cationic amino lipids using a doubly alkylated nucleophilic intermediate to produce a ketone. The ketone, or a corresponding alcohol, is subjected to one or more synthesis steps to add an ionizable moiety thereto. The method can be advantageously employed for the synthesis of unsymmetrical analogues of the above lipids that would be considerably more difficult to make by alternative strategies. The method can also be used to prepare symmetrical ionizable, cationic amino lipids with fewer steps and/or with the use of fewer hazardous chemicals than known synthesis methods.

专利号:US-2012190064-A1
优先权日:2004-10-01
标题 :Feeding buffers, systems, and methods for in vitro synthesis of biomolecules
发明人:KUDLICKI WIESLAW ANTONI; KEPPETIPOLA SHIRANTHI; FLETCHER JULIA; GETBEHEAD ASHLEY ELAINE; KATZEN FEDERICO; VOZZA-BROWN LAURA
权利人:KUDLICKI WIESLAW ANTONI; KEPPETIPOLA SHIRANTHI; FLETCHER JULIA; GETBEHEAD ASHLEY ELAINE; KATZEN FEDERICO; VOZZA-BROWN LAURA; LIFE TECHNOLOGIES CORP
摘要:Compositions, methods and kits for in vitro systems for synthesis of biomolecules such as polypeptides, are provided herein. Cell extracts that provide enhanced yields of soluble proteins using in vitro protein synthesis methods are provided. The invention also includes methods for producing high yields of proteins by the addition of a feeding solution that includes amino acids and an energy source to an ongoing in vitro synthesis system. The invention also includes methods of using a high-yield in vitro synthesis system to produce large quantities of proteins with incorporated labeled amino acids for analysis by methods such as by NMR. The invention further includes vectors for enhanced production of proteins from nucleic acid templates using in vitro synthesis systems.

专利号:US-2011195450-A1
优先权日:2005-09-27
标 题 :In Vitro Protein Synthesis Systems for Membrane Proteins that Include Adolipoproteins and Phospholipid Adolipoprotein Particles
发明人:KUDLICKI WIESLAW; FLETCHER JULIA; KATZEN FEDERICO
权利人:LIFE TECHNOLOGIES CORP
摘要:In vitro protein synthesis systems and methods are provided that produce membrane proteins in soluble form. In some aspects, the invention provides methods of synthesizing proteins using in vitro protein synthesis systems that include an apolipoprotein, in which higher yields of soluble protein are produced than in the absence of the apolipoprotein. Apolipoproteins useful in the present invention include naturally occurring apolipoproteins, as well as sequence variants of wild-type apolipoproteins, and engineered apolipoproteins. The apolipoproteins can be provided in an in vitro protein synthesis system associated with lipid or not associated with lipid. The invention also provides compositions and kits for synthesis of proteins in soluble form, in which the compositions and kits include cell extracts for protein translation and at least one apolipoprotein biomolecule.

专利号:WO-2007038755-A1
优先权日:2005-09-27
标 题:In vitro protein synthesis systems for membrane proteins that include apolipoproteins and phospholipid-apolipoprotein particles
发明人:KUDLICKI WIESLAW; FLETCHER JULIA; KATZEN FEDERICO
权利人:INVITROGEN CORP; KUDLICKI WIESLAW; FLETCHER JULIA; KATZEN FEDERICO
摘要:In vitro protein synthesis systems and methods are provided that produce membrane proteins in soluble form. In some aspects, the invention provides methods of synthesizing proteins using in vitro protein synthesis systems that include an apolipoprotein, in which higher yields of soluble protein are produced than in the absence of the apolipoprotein. Apolipoproteins useful in the present invention include naturally occurring apolipoproteins, as well as sequence variants of wild-type apolipoproteins, and engineered apolipoproteins. The apolipoproteins can be provided in an in vitro protein synthesis system associated with lipid or not associated with lipid. The invention also provides compositions and kits for synthesis of proteins in soluble form, in which the compositions and kits include cell extracts for protein translation and at least one apolipoprotein biomolecule.

专利号:US-6217901-B1
优先权日:1999-05-25
标题:Liposome-assisted synthesis of polymeric nanoparticles
发明人:PERROTT MICHAEL G; BARRY STEPHEN E
权利人:ALNIS LLC
摘要:Synthetic polymer complements (SPCs) are provided, as well as methods for their synthesis and use. The SPCs range in size from about 20 to about 1000 nm. The SPCs have surfaces that are complementary to surface sites of target molecules, resulting in the ability of the SPCs to selectively bind to molecular targets. The molecular recognition capability of these particles enables their use in diagnostic, therapeutic, and separation applications. The SPC is formed by contacting a target template molecule with a set of building blocks solubilized in the interior of a liposome, which building blocks are then polymerized into a network to form the synthetic polymer complement in the interior of the liposome. The target templates are removed to produce complementary sites in a SPC that map the surface of the target, resulting in a water-soluble SPC nanoparticle of similar dimensions as the interior of the liposome that originally supported it and capable of molecular recognition.

专利号:US-9932582-B2
优先权日:2014-01-14
标题 :Materials and methods for modulation of tendon healing
发明人:GILCHRIST DEREK STEWART; MILLAR NEAL LINDSAY
权利人:UNIV GLASGOW COURT
摘要:The invention relates to the use of microRNA 29 and precursors and mimics thereof for the modulation of tendon injury and the biomechanical properties of tendon. In particular, the invention derives from the finding that synthesis of type 1 collagen in tenocytes is less sensitive to miR-29 than is synthesis of type 3 collagen, thus enabling the balance between the collagen subtypes to be modulated in favor of type 1 collagen, mitigating reduction in biomechanical properties during healing.
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主要参考文献

[参考文献]: An T Ngo, Et Al. Membrane Order Parameters For Interdigitated Lipid Bilayers Measured Via Polarized Total-Internal-Reflection Fluorescence Microscopy. Biochim Biophys Acta. 2014 Nov;1838(11):2861-9.
[参考文献]: Deirdre A Costello, Et Al. Variations In Ph Sensitivity, Acid Stability, And Fusogenicity Of Three Influenza Virus H3 Subtypes. J Virol. 2015 Jan;89(1):350-60.
[参考文献]: Dong Woog Lee, Et Al. Real-Time Intermembrane Force Measurements And Imaging Of Lipid Domain Morphology During Hemifusion. Nat Commun. 2015 May 26:6:7238.
[参考文献]: Hema Balakrishna Bhat, Et Al. Evaluation Of Aegerolysins As Novel Tools To Detect And Visualize Ceramide Phosphoethanolamine, A Major Sphingolipid In Invertebrates. Faseb J. 2015 Sep;29(9):3920-34.
[参考文献]: Huong T T Phan, Et Al. Structure-Dependent Interactions Of Polyphenols With A Biomimetic Membrane System. Biochim Biophys Acta. 2014 Oct;1838(10):2670-7.

合成参考文献


参考文献:10.1016/s1388-1981(99)00059-1
摘要:Sugimoto H, Yamashita S. Characterization of the transacylase activity of rat liver 60-kDa lysophospholipase-transacylase. Acyl transfer from the sn-2 to the sn-1 position. Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1999 May;1438(2):264–72. doi: 10.1016/s1388-1981(99)00059-1.
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