(R)-2,3-O-didecanoyl-sn-glycerol | 172588-12-4

• 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: (R)-2,3-O-didecanoyl-sn-glycerol
• 英文别名: 2,3-sn-dicaprin；1,2-dicaproylglycerol；(R)-1,2-didecanoylglycerol；[(2R)-2-decanoyloxy-3-hydroxypropyl] decanoate
• CAS: 172588-12-4
• 化学式: C₂₃H₄₄O₅
• 分子量: 400.599
• InChiKey: GNSDEDOVXZDMKM-OAQYLSRUSA-N

物化性质

• 沸点：
  481.9±12.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  28
• 可旋转键数：
  22
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  对硝基苯酚 、 pentylphosphonic dichloride 、 (R)-2,3-O-didecanoyl-sn-glycerol 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 (S_P)-O-(2,3-O-didecanoyl-sn-glyceryl) O-(p-nitrophenyl) n-pentylphosphonate 、 (R_P)-O-(2,3-O-didecanoyl-sn-glyceryl) O-(p-nitrophenyl) n-pentylphosphonate
  参考文献：
  名称：

  在合成类似于甘油三酯的对映纯膦酸酯中的应用：一类新的脂肪酶抑制剂

  摘要：

  膦酸酯化合物通过与催化丝氨酸形成共价键来模拟在天然底物的酶促羧酸酯水解过程中发生的第一个过渡态。然而，迄今为止，用于抑制研究的有机磷化合物或多或少类似于天然甘油三酯底物。为了阐明脂肪酶的界面活化和作用机制，需要制备特异性抑制剂。为了实现这一目标，从 C-4 手性合成子、3-丁烯-1,2-二醇开始，制备了对映体纯的 sn-1,2- 和 sn-2,3-O-二癸酰基甘油化合物，并用 n -戊基膦酰二氯和对硝基苯酚得到相应的非对映膦酸酯，它们是酰基甘油类似物。随后分离每种膦酸酯非对映异构体 A/B 或 ent-A/ent-B，

  DOI：

  10.1002/(sici)1099-0690(199907)1999:7<1671::aid-ejoc1671>3.0.co;2-z
• 作为产物：
  描述：

  正癸酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (R)-2,3-O-didecanoyl-sn-glycerol
  参考文献：
  名称：

  在合成类似于甘油三酯的对映纯膦酸酯中的应用：一类新的脂肪酶抑制剂

  摘要：

  膦酸酯化合物通过与催化丝氨酸形成共价键来模拟在天然底物的酶促羧酸酯水解过程中发生的第一个过渡态。然而，迄今为止，用于抑制研究的有机磷化合物或多或少类似于天然甘油三酯底物。为了阐明脂肪酶的界面活化和作用机制，需要制备特异性抑制剂。为了实现这一目标，从 C-4 手性合成子、3-丁烯-1,2-二醇开始，制备了对映体纯的 sn-1,2- 和 sn-2,3-O-二癸酰基甘油化合物，并用 n -戊基膦酰二氯和对硝基苯酚得到相应的非对映膦酸酯，它们是酰基甘油类似物。随后分离每种膦酸酯非对映异构体 A/B 或 ent-A/ent-B，

  DOI：

  10.1002/(sici)1099-0690(199907)1999:7<1671::aid-ejoc1671>3.0.co;2-z

文献信息

• Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in an organic solvent system
  作者：Daniel Alberto Sánchez、Gabriela Marta Tonetto、María Luján Ferreira

  DOI：10.1016/j.molcatb.2013.11.010

  日期：2014.2

  In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprin in n-heptane as the reaction medium.

  在这项工作中，固定化形式的1,3-位置选择性脂肪酶（Rhizomucor miehei）催化的甘油与癸酸的酯化反应对于在正庚烷（作为反应介质）中合成1,3-二caprin是有效的。。
• Studies on the substrate specificity of purified human milk lipoprotein lipase
  作者：C. ‐S. Wang、A. Kuksis、F. Manganaro

  DOI：10.1007/bf02534942

  日期：1982.4

  The fatty acid specificity of purified human milk lipoprotein lipase was studied using the C₁₈ to C₅₄ (total acyl carbon number) saturated and the C₅₄ mono‐, di‐ and triunsaturated monoacid triacylglycerols. Kinetic determinations indicated that the medium‐chain triacylglycerols were better substrates than long‐ or very short‐chain saturated triacylglycerols. The unsaturated triacylglycerols were hydrolyzed at rates comparable to that of tricaprylin with triolein having the highest rate of hydrolysis of the unsaturated species tested. The enzyme attacked the primary ester bond much more readily than the secondary ester bond. The purified human milk lipoprotein lipase showed a preferential stereospecific lipolysis of thesn‐1‐position of the triacylglycerol molecule.

  摘要 使用 C18 至 C54（酰基总碳数）饱和和 C54 单酸、双酸和三酸三酰甘油研究了纯化人乳脂蛋白脂肪酶的脂肪酸特异性。动力学测定表明，与长链或极短链饱和三酰甘油相比，中链三酰甘油是更好的底物。不饱和三酰甘油的水解速度与三碳甘油酯的水解速度相当，其中三烯甘油酯的水解速度在所测试的不饱和三酰甘油酯中最高。该酶攻击一级酯键的速度比攻击二级酯键的速度快得多。纯化的人乳脂蛋白脂肪酶对三酰基甘油分子的sn-1位显示出优先的立体特异性脂肪分解作用。
• Enzymatic preparation of enantiomerically pure <i>sn</i> -2,3-diacylglycerols: A stereoselective ethanolysis approach
  作者：Weera Piyatheerawong、Tsuneo Yamane、Hideo Nakano、Yugo Iwasaki

  DOI：10.1007/s11746-006-1245-4

  日期：2006.7

  AbstractStereoselective ethanolysis of monoacid TAG by immobilized Rhizomucor miehei lipase (RML) was studied for preparation of optically pure sn‐2,3‐DAG. Trioctanoylglycerol (TO) was used as a model substrate. The enantiomeric purity of the product, sn‐2,3‐dioctanoylglycerol (sn‐2,3‐DO), was very high (percent enantiomeric excess >99%) when an excess of ethanol was used. The result indicated that RML was highly stereoselective toward the sn‐1 position of TO under conditions of excess ethanol. The stereoselectivity of RML depended on the amount of ethanol. The larger the amount of ethanol was, the higher the stereoselectivity became. After optimizing the parameters such as reactant molar ratio, water content, and temperature, (ethanol/TO molar ratio =31∶1 and water content =7.5 wt% of the reactants at 25°C), optically pure sn‐2,3‐DO was obtained at 61.1 mol% in the glyceride fraction in 20 min. The above conditions were further applied for ethanolysis of monoacid TAG with different acyl groups such as tridecanoylglycerol (C10∶0), tridodecanoylglycerol (C12∶0), tritetradecanoylglycerol (C14∶0) and trioctadecenoylglycerol [triolein, (C18∶1)]. The yields and enantiomeric purities of 1,2(2,3)‐DAG were dramatically reduced when TAG with FA longer than decanoic acid were used.
• A novel extracellular esterase from Bacillus subtilis and its conversion to a monoacylglycerol hydrolase
  作者：Thorsten Eggert、Gaëlle Pencreac‘h、Isabelle Douchet、Robert Verger、Karl-Erich Jaeger

  DOI：10.1046/j.1432-1327.2000.01736.x

  日期：2000.11

  A novel gene lipB, which encodes an extracellular lipolytic enzyme, was identified in the Bacillus subtilis genomic DNA sequence. We have cloned and overexpressed lipB in B. subtilis and Escherichia coli and have also purified the enzyme from a B. subtilis culture supernatant to electrophoretic homogeneity. Four different lipase assays were used to determine its catalytic activity: pH‐stat, spectrophotometry, fluorimetry and the monomolecular film technique. LipB preferentially hydrolysed triacylglycerol‐esters and p‐nitrophenyl‐esters of fatty acids with short chain lengths of ≤ 10 carbon atoms. Triolein, which is a typical substrate for true lipases, was not hydrolysed at all. These results led us to classify LipB as an esterase rather than a lipase. The catalytic triad of LipB consists of residues Ser78, Asp134, and His157 as demonstrated by amino‐acid sequence alignments and site‐directed mutagenesis. The nucleophile Ser78 is located in a lipase‐specific consensus sequence, which is Ala‐X‐Ser‐X‐Gly for most Bacillus lipases. All other bacterial lipases contain a glycine residue instead of the alanine at position‐2 with respect to the catalytic serine. We have investigated the role of this alanine residue by constructing LipB variant A76G, thereby restoring the lipase‐specific consensus motif. When compared with LipB this variant showed a markedly reduced thermostability but an increased stability at pH 5–7. Determination of the specific activities of wild‐type LipB and variant A76G using a monomolecular film of the substrate monoolein revealed an interesting result: the A76G substitution had converted the esterase LipB into a monoacylglycerol hydrolase.
• Application to the Synthesis of Enantiopure Phosphonates Analogous to Triglycerides: A New Class of Inhibitors of Lipases
  作者：Frank Marguet、Jean-François Cavalier、Robert Verger、Gérard Buono

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1671::aid-ejoc1671>3.0.co;2-z

  日期：1999.7

  3-O-didecanoylglycerol compounds were prepared – starting from a C-4 chiral synthon, 3-buten-1,2-diol – and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be

  膦酸酯化合物通过与催化丝氨酸形成共价键来模拟在天然底物的酶促羧酸酯水解过程中发生的第一个过渡态。然而，迄今为止，用于抑制研究的有机磷化合物或多或少类似于天然甘油三酯底物。为了阐明脂肪酶的界面活化和作用机制，需要制备特异性抑制剂。为了实现这一目标，从 C-4 手性合成子、3-丁烯-1,2-二醇开始，制备了对映体纯的 sn-1,2- 和 sn-2,3-O-二癸酰基甘油化合物，并用 n -戊基膦酰二氯和对硝基苯酚得到相应的非对映膦酸酯，它们是酰基甘油类似物。随后分离每种膦酸酯非对映异构体 A/B 或 ent-A/ent-B，