1,3-didocosahexaenoylglycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-didocosahexaenoylglycerol
• 英文别名: (4'Z,7'Z,10'Z,13'Z,16'Z,19'Z)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid, diester with 1,2,3-propanetriol；[3-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyl]oxy-2-hydroxypropyl] (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate
• 化学式: C₄₇H₆₈O₅
• 分子量: 713.054
• InChiKey: MXYFTPKXCFFQRG-GZSOIYOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  52
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-didocosahexaenoylglycerol 、 己酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到1,3-didocosahexaenoyl-2-hexanoylglycerol
  参考文献：
  名称：

  拥有EPA和DHA在其终端位置反转结构的甘油三酯的合成

  摘要：

  本报告描述了LML型的反转结构的三酰基甘油（标签）的合成，具有纯EPA或DHA位于与纯偶数沿甘油骨架的终端1,3位饱和脂肪酸（C6：0-C16：0 ）占据2位。这些化合物通过包括高度选择性固定化的两步化学酶促合成路线合成南极假丝酵母脂肪酶掺入EPA或DHA激活为丙酮肟酯专门为甘油的1,3-位置。随后通过EDCI偶联剂将饱和的脂肪酰基引入剩余的2-位，以高效地完成标题化合物。这是具有上的长链n-3多不饱和脂肪酸的结构颠倒的标签的第一份报告。可以预期的是，这些新的化合物和它们的合成方法将找到的各种重要的用途，例如分析标准，筛选生物活性和在作为前药制药领域。

  DOI：

  10.1016/j.tet.2015.09.034
• 作为产物：
  描述：

  二十二碳六烯酸 在 4-二甲氨基吡啶 、 C_. antarctica lipase 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,3-didocosahexaenoylglycerol
  参考文献：
  名称：

  Activation of n-3 polyunsaturated fatty acids as oxime esters: a novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase

  摘要：

  A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-allcylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields. (C) 2012 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2012.07.005

文献信息

• One-pot synthesis of polyunsaturated fatty acid amides with anti-proliferative properties
  作者：Hugo Tremblay、Catherine St-Georges、Marc-André Legault、Caroline Morin、Samuel Fortin、Eric Marsault

  DOI：10.1016/j.bmcl.2014.10.084

  日期：2014.12

  A one-pot environmentally friendly transamidation of ω-3 fatty acid ethyl esters to amides and mono- or diacylglycerols was investigated via the use of a polymer-supported lipase. The method was used to synthesize a library of fatty acid monoglyceryl esters and amides. These new derivatives were found to have potent growth inhibition effects against A549 lung cancer cells.

  通过使用聚合物支持的脂肪酶，研究了一锅环保的ω-3脂肪酸乙酯向酰胺和单或二酰基甘油的氨基转移。该方法用于合成脂肪酸单甘油酯和酰胺的文库。发现这些新的衍生物对A549肺癌细胞具有有效的生长抑制作用。
• Synthesis of triacylglycerol from polyunsaturated fatty acid by immobilized lipase
  作者：Yoshitsugu Kosugi、Naoki Azuma

  DOI：10.1007/bf02541362

  日期：1994.12

  More than 95% of polyunsaturated acid (PUFA) was converted to triacylglycerol by immobilized lipase fromCandida antarctica orRhizomucor miehei. The esterification was carried out at 50–60°C with shaking and dehydration for 24 h. The substrates consisted of glycerol and free fatty acid or ethyl esters of the fatty acid at a 1∶3 molar ratio. The docosahexaenoic acid (DHA) or eicosapentaenoic acid (EPA) in the substrate polymerized during the reaction, and they required 5–10% more than the stoichiometric amount to compensate for the PUFA loss. On the contrary, ethyl esters of DHA and EPA were not polymerized. Pure tridocosahexaenoyl, trieicosapentaenoly and triarachidonoyl glycerol were isolated after passing the product through a basic aluminum oxide column. Industrial feasibility of this process was discussed for the ethyl ester as substrate.

  摘要 利用固定化脂肪酶将95%以上的多不饱和脂肪酸（PUFA）转化为三酰甘油。底物包括甘油和游离脂肪酸或脂肪酸乙酯，摩尔比为 1∶3。底物中的二十二碳六烯酸（DHA）或二十碳五烯酸（EPA）在反应过程中聚合，它们需要比化学计量量多 5-10% 的量来补偿 PUFA 的损失。相反，DHA 和 EPA 的乙酯没有聚合。产品通过碱性氧化铝柱后，分离出了纯净的三二十六烯酰、三二十五烯酰和三丙烯酰甘油。讨论了以乙酯为底物进行该工艺的工业可行性。
• Synthesis of reversed structured triacylglycerols possessing EPA and DHA at their terminal positions
  作者：Anna V. Gudmundsdottir、Kai-Anders Hansen、Carlos D. Magnusson、Gudmundur G. Haraldsson

  DOI：10.1016/j.tet.2015.09.034

  日期：2015.11

  EPA or DHA activated as acetoxime esters exclusively into the 1,3-positions of glycerol. The saturated fatty acyl groups were subsequently introduced to the remaining 2-position by EDCI coupling agent to accomplish the title compounds highly efficiently. This is the first report on reversed structured TAGs possessing the long-chain n-3 polyunsaturated fatty acids. It is anticipated that these novel

  本报告描述了LML型的反转结构的三酰基甘油（标签）的合成，具有纯EPA或DHA位于与纯偶数沿甘油骨架的终端1,3位饱和脂肪酸（C6：0-C16：0 ）占据2位。这些化合物通过包括高度选择性固定化的两步化学酶促合成路线合成南极假丝酵母脂肪酶掺入EPA或DHA激活为丙酮肟酯专门为甘油的1,3-位置。随后通过EDCI偶联剂将饱和的脂肪酰基引入剩余的2-位，以高效地完成标题化合物。这是具有上的长链n-3多不饱和脂肪酸的结构颠倒的标签的第一份报告。可以预期的是，这些新的化合物和它们的合成方法将找到的各种重要的用途，例如分析标准，筛选生物活性和在作为前药制药领域。
• Activation of n-3 polyunsaturated fatty acids as oxime esters: a novel approach for their exclusive incorporation into the primary alcoholic positions of the glycerol moiety by lipase
  作者：Carlos D. Magnusson、Gudmundur G. Haraldsson

  DOI：10.1016/j.chemphyslip.2012.07.005

  日期：2012.10

  A novel approach has been developed for activating the highly bioactive long-chain n-3 polyunsaturated fatty acids EPA and DHA as oxime esters and incorporating them exclusively to the end-positions of glycerol and enantiopure 1-O-allcylglycerols. The Candida antarctica lipase B was observed to display a superb regioselectivity when using the acetoxime esters of EPA and DHA as acyldonors under mild condition to keep acyl-migration side-reaction under complete control. Regiopure 1,3-diacylglycerols, 1-O-alkyl-3-acyl-sn-glycerols and their antipodes possessing EPA and DHA were afforded in very high purity and yields. (C) 2012 Elsevier Ireland Ltd. All rights reserved.