1,2-O-dipalmitoyl-3-O-dimethoxytritylglycerol

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2-O-dipalmitoyl-3-O-dimethoxytritylglycerol
• 英文别名: [3-[bis(4-methoxyphenyl)-phenylmethoxy]-2-hexadecanoyloxypropyl] hexadecanoate
• 化学式: C₅₆H₈₆O₇
• 分子量: 871.295
• InChiKey: APVXLDKRIYVTJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.43
• 重原子数：
  63.0
• 可旋转键数：
  39.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,2-O-dipalmitoyl-3-O-dimethoxytritylglycerol 在 Amberlite IR-120H resin 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.5h， 生成 1,2-二棕榈酰-rac-丙三醇
  参考文献：
  名称：

  Lipidomics Characterization of Biosynthetic and Remodeling Pathways of Cardiolipins in Genetically and Nutritionally Manipulated Yeast Cells

  摘要：

  Cardioipins (CLs) are unique tetra-acylated phospholipids of mitochondria and define the bioenergetics, and regulatory functions of these organelles. An unresolved paradox is the high uniformity of CL molecular species (tetra-linoleoyl-CL) in the heart, liver, and skeletal muscles in contrast to their high diversification in the brain. Here, we combined liquid chromatography mass-spectrometry -based phospholipidomics with genetic, and nutritional manipulations to explore CLs biosynthetic Vs postsynthetic remodeling processes in S. cerevisiae yeast cells. By applying the differential phospholipidomics analysis, we evaluated the contribution of Cld1 (CL-specific phospholipase A) and Taz1 (acyl-transferase) as the major regulatory mechanisms of the remodeling process. We further established that nutritional "pressure" by high levels of free fatty acids triggered a massive synthesis of homoacylated molecular species in all classes of phospholipids, resulting in the preponderance of the respective, homoacylated CLs. We found that changes in molecular speciation of CLs induced by exogenous C18-fatty acid's,(C18:1 and C18:2) Wild-type (wt) cells did not occur in any of the remodeling mutant cells, including dd1 Delta, taz1 Delta, and dd1 Delta taz1 Delta. Interestingly, molecular speciation of CLs in wt and double mutant cells dd1 Delta taz1 Delta was markedly different. Given that the bioenergetics functions are preserved in the, double mutant, this suggests that the accumulated MLCL-rather than the changed CL speciation-are the likely major Contributors to the mitochondrial dysfunction in taz1 Delta mutant cells (also characteristic of Barth syndrome): Biochemical studies of Cld1 specificity and computer modeling confirmed the hydrolytic selectivity of the enzyme toward C16-CL substrates and the preservation of C18:1-containing CL species.

  DOI：

  10.1021/acschembio.6b00995
• 作为产物：
  描述：

  甘油棕榈酸酯 在 吡啶 、 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 17.5h， 生成 1,2-O-dipalmitoyl-3-O-dimethoxytritylglycerol
  参考文献：
  名称：

  Lipidomics Characterization of Biosynthetic and Remodeling Pathways of Cardiolipins in Genetically and Nutritionally Manipulated Yeast Cells

  摘要：

  Cardioipins (CLs) are unique tetra-acylated phospholipids of mitochondria and define the bioenergetics, and regulatory functions of these organelles. An unresolved paradox is the high uniformity of CL molecular species (tetra-linoleoyl-CL) in the heart, liver, and skeletal muscles in contrast to their high diversification in the brain. Here, we combined liquid chromatography mass-spectrometry -based phospholipidomics with genetic, and nutritional manipulations to explore CLs biosynthetic Vs postsynthetic remodeling processes in S. cerevisiae yeast cells. By applying the differential phospholipidomics analysis, we evaluated the contribution of Cld1 (CL-specific phospholipase A) and Taz1 (acyl-transferase) as the major regulatory mechanisms of the remodeling process. We further established that nutritional "pressure" by high levels of free fatty acids triggered a massive synthesis of homoacylated molecular species in all classes of phospholipids, resulting in the preponderance of the respective, homoacylated CLs. We found that changes in molecular speciation of CLs induced by exogenous C18-fatty acid's,(C18:1 and C18:2) Wild-type (wt) cells did not occur in any of the remodeling mutant cells, including dd1 Delta, taz1 Delta, and dd1 Delta taz1 Delta. Interestingly, molecular speciation of CLs in wt and double mutant cells dd1 Delta taz1 Delta was markedly different. Given that the bioenergetics functions are preserved in the, double mutant, this suggests that the accumulated MLCL-rather than the changed CL speciation-are the likely major Contributors to the mitochondrial dysfunction in taz1 Delta mutant cells (also characteristic of Barth syndrome): Biochemical studies of Cld1 specificity and computer modeling confirmed the hydrolytic selectivity of the enzyme toward C16-CL substrates and the preservation of C18:1-containing CL species.

  DOI：

  10.1021/acschembio.6b00995

文献信息

• Lipidomics Characterization of Biosynthetic and Remodeling Pathways of Cardiolipins in Genetically and Nutritionally Manipulated Yeast Cells
  作者：Yulia Y. Tyurina、Wenjia Lou、Feng Qu、Vladimir A Tyurin、Dariush Mohammadyani、Jenney Liu、Maik Hüttemann、Michael A. Frasso、Peter Wipf、Hülya Bayir、Miriam. L. Greenberg、Valerian E. Kagan

  DOI：10.1021/acschembio.6b00995

  日期：2017.1.20

  Cardioipins (CLs) are unique tetra-acylated phospholipids of mitochondria and define the bioenergetics, and regulatory functions of these organelles. An unresolved paradox is the high uniformity of CL molecular species (tetra-linoleoyl-CL) in the heart, liver, and skeletal muscles in contrast to their high diversification in the brain. Here, we combined liquid chromatography mass-spectrometry -based phospholipidomics with genetic, and nutritional manipulations to explore CLs biosynthetic Vs postsynthetic remodeling processes in S. cerevisiae yeast cells. By applying the differential phospholipidomics analysis, we evaluated the contribution of Cld1 (CL-specific phospholipase A) and Taz1 (acyl-transferase) as the major regulatory mechanisms of the remodeling process. We further established that nutritional "pressure" by high levels of free fatty acids triggered a massive synthesis of homoacylated molecular species in all classes of phospholipids, resulting in the preponderance of the respective, homoacylated CLs. We found that changes in molecular speciation of CLs induced by exogenous C18-fatty acid's,(C18:1 and C18:2) Wild-type (wt) cells did not occur in any of the remodeling mutant cells, including dd1 Delta, taz1 Delta, and dd1 Delta taz1 Delta. Interestingly, molecular speciation of CLs in wt and double mutant cells dd1 Delta taz1 Delta was markedly different. Given that the bioenergetics functions are preserved in the, double mutant, this suggests that the accumulated MLCL-rather than the changed CL speciation-are the likely major Contributors to the mitochondrial dysfunction in taz1 Delta mutant cells (also characteristic of Barth syndrome): Biochemical studies of Cld1 specificity and computer modeling confirmed the hydrolytic selectivity of the enzyme toward C16-CL substrates and the preservation of C18:1-containing CL species.