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1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine | 159407-32-6

中文名称
——
中文别名
——
英文名称
1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine
英文别名
sn1-lyso-PC-DHA;sn1-lysoPCDHA;lysoPCDHA;2-Docosahexaenoyl-sn-glycero-3-phosphocholine(~90%);[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-3-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine化学式
CAS
159407-32-6
化学式
C30H50NO7P
mdl
——
分子量
567.703
InChiKey
FTLVGMFFHDRYDI-APPDJCNMSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    4.6
  • 重原子数:
    39
  • 可旋转键数:
    24
  • 环数:
    0.0
  • sp3杂化的碳原子比例:
    0.57
  • 拓扑面积:
    105
  • 氢给体数:
    1
  • 氢受体数:
    7

反应信息

  • 作为反应物:
    描述:
    1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine 、 5-(3,5-bis(triisopropylsilyloxy)phenoxy)-5-oxopentanoic acid 在 4-二甲氨基吡啶N,N'-二环己基碳二亚胺 作用下, 以 二氯甲烷 为溶剂, 反应 24.0h, 以65%的产率得到1-[5-(3,5-bis(triisopropylsilyloxy)phenoxy)-5-oxopentanoyl]-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine
    参考文献:
    名称:
    多不饱和脂肪酸-苯酚结合物作为抗羰基应激脂酚的合成与评价
    摘要:
    羰基和氧化应激在各种神经退行性疾病中发挥着重要作用,例如阿尔茨海默病、帕金森病和年龄相关性黄斑变性 (AMD)。在视网膜病变中,这两种机制都参与了全反式视黄醛(AtR,反应性醛)向双类视黄醇 A2E 的转化。由于 AtR 和 A2E 的积累有助于光感受器细胞凋亡,我们设计并合成了一系列具有增强的抗羰基应力特性的 O-烷基化间苯二酚衍生物。此外,这些酚结构与多不饱和脂肪酸如二十二碳六烯酸 (C22:6 n-3; DHA) 或溶血磷脂酰胆碱-DHA 结合物相连,以专门增加它们的生物利用度,从而靶向视网膜。间苯三酚-DHA、白藜芦醇-DHA的选择性合成,
    DOI:
    10.1002/ejoc.201402282
  • 作为产物:
    描述:
    PC-16:0-DHA 在 Mucor miehei lipozyme 、 作用下, 以 乙醇 为溶剂, 反应 29.0h, 以85%的产率得到1-lyso-2-docosahexaenoyl-sn-glycero-3-phosphatidylcholine
    参考文献:
    名称:
    [EN] NEW LIPOPHENOL COMPOUNDS AND USES THEREOF
    [FR] NOUVEAUX COMPOSÉS DE LIPOPHÉNOL ET LEURS UTILISATIONS
    摘要:
    本发明涉及一种具有式(I)的化合物,其中:- i为0或1;j为0或1;k为0或1;- R1和R2特别是H,(C1-C12)烷基,或者具有式C(O)R的基团;- R是具有至少19个碳原子的直链或支链烷基基团;- R3为H且当j=1时k=0;或者当j=0时,R3为-C(O)R或-L-C(O)R;- L、U和L"为连接基;其中,当j=0时,R1、R2和R3中至少一个含有基团R。
    公开号:
    WO2015162265A1
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文献信息

  • Determinants of pH profile and acyl chain selectivity in lysosomal phospholipase A2 [S]
    作者:Vania Hinkovska-Galcheva、Robert Kelly、Kelly A. Manthei、Renee Bouley、Wenmin Yuan、Anna Schwendeman、JohnJ.G. Tesmer、James A. Shayman
    DOI:10.1194/jlr.m084012
    日期:——
    Lysosomal phospholipase A2 (LPLA2) is characterized by broad substrate recognition, peak activity at acidic pH, and the transacylation of lipophilic alcohols, especially N-acetyl-sphingosine. Prior structural analysis of LPLA2 revealed the presence of an atypical acidic residue, Asp13, in the otherwise hydrophobic active site cleft. We hypothesized that Asp13 contributed to the pH profile and/or substrate
    溶酶体磷脂酶A2(LPLA2)的特征是广泛的底物识别,在酸性pH下具有峰值活性以及亲脂性醇(尤其是N-乙酰基-鞘氨醇)的酰基转移。LPLA2的先前结构分析显示,在否则为疏水活性位点的裂口中存在非典型酸性残基Asp13。我们假设Asp13有助于pH谱和/或LPLA2对不饱和酰基链的底物偏爱。为了验证这一假设,我们用Asp13取代了丙氨酸,半胱氨酸或苯丙氨酸。然后,我们监测了1-O-酰基-N-乙酰基鞘氨醇的形成,以测量各种甘油磷脂上sn-1和sn-2酰基的水解情况。在中性pH值下,用Asp13取代产生显着的酶活性(7。4)并干扰了单不饱和和双不饱和酰基链的选择性。但是,该位置在选择酰基受体或甘油磷脂的头基中没有明显作用。我们的模型表明,Asp13及其取代基通过形成易碎的酰基链所占据的疏水轨道的一部分,有助于LPLA2的pH活性曲线和酰基链选择性。
  • Positional specificity of lysosomal phospholipase A2
    作者:Akira Abe、Miki Hiraoka、James A. Shayman
    DOI:10.1194/jlr.m600183-jlr200
    日期:2006.10
    5-fold higher than that of 1-O-palmitoyl-NAS. Thus, Lpla2 can act on acyl groups at both sn-1 and sn-2 positions of POPC and OPPC. When 1-palmitoyl-2-unsaturated acyl-sn-glycero-3-phosphocholines were used as acyl donors, the transacylation of the acyl group from the sn-2 position to NAS was preferred to that of the palmitoyl group from the sn-1 position. An exception was observed for 1-palmitoyl-2-ar
    溶酶体磷脂酶A(2)(Lpla2)在肺泡巨噬细胞中高度表达,并可能介导表面活性剂的磷脂代谢。对这种磷脂酶特性的研究与磷脂酶A(1)和磷脂酶A(2)活性的存在是一致的。通过生产由Lpla2的转酰酶活性产生的O-酰基化合物来研究这些活性。将含有POPC和N-乙酰基鞘氨醇(NAS)的脂质体与从稳定转染了小鼠Lpla2基因的MDCK细胞获得的可溶性级分一起孵育。Lpla2生产了两个1-O-酰基-NAS,1-O-棕榈酰基-NAS和1-O-油酰基-NAS。1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的2.5倍。当使用1-油酰基-2-棕榈酰基-sn-甘油-3-磷酸胆碱(OPPC)时,1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的5倍。因此,Lpla2可以在POPC和OPPC的sn-1和sn-2位置同时作用于酰基。当使用1-棕榈酰基-2-不饱和酰基-sn-甘油-3-磷酸胆碱作为
  • Metabolomics annotates ABHD3 as a physiologic regulator of medium-chain phospholipids
    作者:Jonathan Z Long、Justin S Cisar、David Milliken、Sherry Niessen、Chu Wang、Sunia A Trauger、Gary Siuzdak、Benjamin F Cravatt
    DOI:10.1038/nchembio.659
    日期:2011.11
    An untargeted metabolomics approach identifies C14 phosphatidylcholines (PCs) as specific cellular medium-chain substrates of the lipase ABHD3, as well as C5–C8 short-chain PCs including oxidized pro-atherosclerotic and pro-apoptotic PC phospholipids. All organisms, including humans, possess a huge number of uncharacterized enzymes. Here we describe a general cell-based screen for enzyme substrate discovery by untargeted metabolomics and its application to identify the protein α/β-hydrolase domain–containing 3 (ABHD3) as a lipase that selectively cleaves medium-chain and oxidatively truncated phospholipids. Abhd3−/− mice possess elevated myristoyl (C14)-phospholipids, including the bioactive lipid C14-lysophosphatidylcholine, confirming the physiological relevance of our substrate assignments.
    一种非靶向代谢组学方法发现,C14磷脂酰胆碱(PC)是脂肪酶ABHD3的特异性细胞中链底物,还发现了C5âC8短链PC,包括氧化的促动脉粥样硬化和促凋亡PC磷脂。 包括人类在内的所有生物体都拥有大量未定性的酶。在这里,我们描述了一种通过非靶向代谢组学发现酶底物的通用细胞筛选方法,以及该方法在鉴定含δ/δ²-水解酶结构域的蛋白δ/δ²-水解酶结构域3(ABHD3)的应用,该蛋白δ/δ²-水解酶结构域3(ABHD3)是一种选择性裂解中链和氧化截短磷脂的脂肪酶。ABHD3â/â小鼠的肉豆蔻酰(C14)-磷脂含量升高,其中包括生物活性脂质C14-赖磷脂酰胆碱,这证实了我们底物分配的生理相关性。
  • The Highly Selective Production of 2-Arachidonoyl Lysophosphatidylcholine Catalyzed by Purified Calcium-independent Phospholipase A2γ
    作者:Wei Yan、Christopher M. Jenkins、Xianlin Han、David J. Mancuso、Harold F. Sims、Kui Yang、Richard W. Gross
    DOI:10.1074/jbc.m502358200
    日期:2005.7
    Herein, we report the heterologous expression of the human peroxisomal 63-kDa calcium-independent phospholipase A(2)gamma (iPLA(2)gamma) isoform in Sf9 cells, purification of the N-terminal His-tagged enzyme by affinity chromatography, and the identification of its remarkable substrate selectivity that results in the highly selective generation of 2-arachidonoyl lysophosphatidylcholine. Mass spectrometric analyses demonstrated that purified iPLA(2)gamma hydrolyzed saturated or monounsaturated aliphatic groups readily from either the sn-1 or sn-2 positions of phospholipids. In addition, purified iPLA(2)gamma effectively liberated arachidonic acid from the sn-2 position of plasmenylcholine substrates. In contrast, incubation of iPLA(2)gamma with 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine resulted in the rapid release of palmitic acid and the selective accumulation of 2-arachidonoyl lysophosphatidylcholine (LPC), which was not metabolized further by iPLA(2)gamma. The putative regiospecificity of the 2-arachidonoyl LPC product was authenticated by its diagnostic fragmentation pattern during tandem mass spectrometric analysis. To identify the physiological relevance of iPLA(2)gamma-mediated 2-arachidonoyl LPC production utilizing naturally occurring membranes, we incubated purified rat hepatic peroxisomes with iPLA(2)gamma and similarly identified the selective accumulation of 2-arachidonoyl LPC. Furthermore, tandem mass spectrometric analysis demonstrated that 2-arachidonoyl LPC is a natural product in human myocardium, a tissue in which iPLA(2)gamma expression is robust. Because 2-arachidonoyl LPC represents a key branch point intermediate that can potentially lead to a variety of bioactive molecules in eicosanoid signaling (e.g. arachidonic acid, 2-arachidonoylglycerol), these results have uncovered a novel eicosanoid selective pathway through iPLA(2)gamma-mediated 2-arachidonoyl LPC production to amplify and diversify the repertoire of biologic lipid second messengers in response to cellular stimulation.
  • Synthesis and Evaluation of Polyunsaturated Fatty Acid-Phenol Conjugates as Anti-Carbonyl-Stress Lipophenols
    作者:Céline Crauste、Claire Vigor、Philippe Brabet、Madeleine Picq、Michel Lagarde、Christian Hamel、Thierry Durand、Joseph Vercauteren
    DOI:10.1002/ejoc.201402282
    日期:2014.7
    apoptosis, we designed and synthesized a series of O-alkylated resorcinol derivatives featuring enhanced anti-carbonyl-stress properties. Additionally, these phenolic structures are linked to a polyunsaturated fatty acid such as docosahexaenoic acid (C22:6 n-3; DHA) or to a lysophosphatidylcholine–DHA conjugate, in order to specifically increase their bioavailability, and thus, to target the retina. Selective
    羰基和氧化应激在各种神经退行性疾病中发挥着重要作用,例如阿尔茨海默病、帕金森病和年龄相关性黄斑变性 (AMD)。在视网膜病变中,这两种机制都参与了全反式视黄醛(AtR,反应性醛)向双类视黄醇 A2E 的转化。由于 AtR 和 A2E 的积累有助于光感受器细胞凋亡,我们设计并合成了一系列具有增强的抗羰基应力特性的 O-烷基化间苯二酚衍生物。此外,这些酚结构与多不饱和脂肪酸如二十二碳六烯酸 (C22:6 n-3; DHA) 或溶血磷脂酰胆碱-DHA 结合物相连,以专门增加它们的生物利用度,从而靶向视网膜。间苯三酚-DHA、白藜芦醇-DHA的选择性合成,
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同类化合物

钙(2R)-2,3-二(棕榈酰氧基)丙基磷酸酯 辛酸(1R)-1-[(磷酰氧基)甲基]-1,2-乙二基酯单钠盐 血小板活化因子 (C18) 血小板-活化因子C18 苯甲醇,2-甲氧基-5-甲基-a-[1-(甲基氨基)乙基]- 苯甲基(2R)-2-(羟甲基)吡咯烷-1-羧酸酯 苯(甲)醛,2-甲基-4-硝基- 胞苷二磷酸甘油酯 胞苷-5’-二磷酸甘油酯二钠盐 肉豆蔻酰基溶血磷脂胆碱 聚乙二醇单甲醚-2000-二十八烷基磷脂酰乙醇胺 磷酸二氢1,3-羟基-2-丙酯 磷酸,单[3-(十八烷氧基)-2-(苯基甲氧基)丙基]单[2-(1-吡咯烷基)乙基]酯 磷酯酰乙醇胺 磷脂酰胆碱(大豆) 磷脂酰肌醇 磷脂酰乙醇胺(牛脑) 磷脂酰乙醇胺(大豆) 磷脂酰丝氨酸 硬脂酰溶血卵磷脂 甲氧基聚乙二醇-二棕榈酰磷酯酰乙醇胺 甘磷酸胆碱 甘油磷酸镁 甘油磷酸锌 甘油磷酸铁 甘油磷酸钾 甘油磷酸钾 甘油磷酸钠 甘油磷酸钙盐 甘油磷酸酯镍(2+)盐 甘油磷酸酯锰盐 甘油磷酸酯 甘油磷酸水和物 甘油磷酸-N-花生四烯酸乙醇胺 甘油磷酸-N-油酰基乙醇胺 甘油磷酸-N-棕榈酰乙醇胺 甘油磷酰丝氨酸 琥珀酸)氢21-羟基-5&#x3B2-孕烷-3,20-二酮21-( 焦磷酸甘油油酰甘油(铵盐) 溶血磷脂酰胆碱(鸡蛋) 溶血卵磷脂(猪或牛肝) 氨基甲酰-PAF(C16) 氢化磷脂酰胆碱 氢化卵磷脂 月桂酰溶血磷酰脂 心磷脂(钠盐或铵盐) 大豆卵磷脂 外消旋-1,2-二月桂酰-甘油-3-磷酰-胆碱 叔-丁氧基羰基-脯氨酰-氨基琥珀酰<丁二酰>-甘氨酰-丙氨酸甲基酯 反-N-(1-(2-乙氧基乙基)-3-甲基-4-哌啶基)-N-苯基苯酰胺