1-O-oleoyl-2-O-palmitoyl-sn-glycerol | 64199-61-7

• 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-O-oleoyl-2-O-palmitoyl-sn-glycerol
• 英文别名: 1-O-oleyl-2-O-palmitoyl-sn-glycerol；1-Oleoyl-2-palmitoyl-sn-glycerol；[(2S)-2-hexadecanoyloxy-3-hydroxypropyl] (Z)-octadec-9-enoate
• CAS: 64199-61-7
• 化学式: C₃₇H₇₀O₅
• 分子量: 594.96
• InChiKey: DOZKMFVMCATMEH-OZKTZCCCSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  14.2
• 重原子数：
  42
• 可旋转键数：
  35
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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-O-oleoyl-2-O-palmitoyl-sn-glycerol 、 2,3,4,6-tetra-O-tetramethylsilyl-α-D-galactopyranosyl iodide 在 4 A molecular sieve 、 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 40.0h， 以72%的产率得到1-O-oleoyl-2-O-palmitoyl-3-O-α-D-galactopyranosyl-sn-glycerol
  参考文献：
  名称：

  Efficient, one-pot syntheses of biologically active α-linked glycolipids

  摘要：

  过 O-硅烷基化的半乳糖碘化物与完全功能化的糖脂发生δ-糖苷化反应，生成与生物相关的共轭物。

  DOI：

  10.1039/b702551c
• 作为产物：
  描述：

  1-O-(9z)-octadenoyl-3-benzylglycerol 在 4-二甲氨基吡啶 、 三氯化硼 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.75h， 生成 1-O-oleoyl-2-O-palmitoyl-sn-glycerol
  参考文献：
  名称：

  Efficient, one-pot syntheses of biologically active α-linked glycolipids

  摘要：

  过 O-硅烷基化的半乳糖碘化物与完全功能化的糖脂发生δ-糖苷化反应，生成与生物相关的共轭物。

  DOI：

  10.1039/b702551c

文献信息

• Alternative splicing of the human diacylglycerol kinase ζ gene in muscle
  作者：Li Ding、Michaeline Bunting、Matthew K. Topham、Thomas M. McIntyre、Guy A. Zimmerman、Stephen M. Prescott

  DOI：10.1073/pnas.94.11.5519

  日期：1997.5.27

  Diacylglycerol can function as a second messenger, and one mechanism for the attenuation of this signal is its conversion to phosphatidic acid, which is catalyzed by diacylglycerol kinase (DGK). We screened a cDNA library from human skeletal muscle and isolated two DGKζ cDNAs that differed from the 3.5-kb clone originally identified in endothelial cells. One transcript, which was 3.4 kb long, was shown to be nonfunctional; it had a 77-bp deletion that included the translation initiation site. The other was 4.1 kb long with a unique 5′ sequence of 853 bp. We also isolated a genomic clone of DGKζ and determined its organization and location; it contains 32 exons, spans approximately 50 kb of genomic sequence, and maps to chromosome 11p11.2. The protein encoded by the 4.1-kb transcript contains two cysteine-rich regions, a catalytic domain, and ankyrin repeats like the endothelial form of DGKζ, as well as a unique N-terminal domain. The coding sequence was shown to be derived from alternative splicing of the DGKζ gene. In cells transfected with the 4.1-kb clone, we detected a 130-kDa protein with an antibody to DGKζ and demonstrated that it was localized predominantly in the nucleus. We conclude that alternative splicing generates tissue-specific variants of DGKζ that share some properties but may have unique ones as well.

  Diacylglycerol可以作为第二信使，其信号的衰减机制之一是其被Diacylglycerol激酶（DGK）催化转化为磷酸甘油酸。我们筛选了来自人类骨骼肌的cDNA文库，并分离出两个DGKζ cDNA，它们与最初在内皮细胞中鉴定的3.5 kb克隆不同。其中一个转录本长3.4 kb，被证明是非功能性的；它有一个包括翻译起始位点的77 bp缺失。另一个长4.1 kb，具有853 bp的独特5'序列。我们还分离了DGKζ的基因组克隆，并确定了其组织和位置；它包含32个外显子，跨越大约50 kb的基因组序列，并映射到11p11.2染色体。由4.1 kb转录本编码的蛋白质包含两个富含半胱氨酸的区域、一个催化域和类似内皮细胞DGKζ的ankyrin重复序列，以及一个独特的N端域。编码序列被证明是由DGKζ基因的可变剪接所导致的。在转染了4.1 kb克隆的细胞中，我们检测到一个130 kDa的DGKζ抗体蛋白，并证明它主要定位于细胞核。我们得出结论，可变剪接产生了DGKζ的组织特异性变异体，它们具有一些共同的特性，但也可能具有独特的特性。
• Two types of MGDG synthase genes, found widely in both 16:3 and 18:3 plants, differentially mediate galactolipid syntheses in photosynthetic and nonphotosynthetic tissues in <i>Arabidopsis thaliana</i>
  作者：Koichiro Awai、Eric Maréchal、Maryse A. Block、Delphine Brun、Tatsuru Masuda、Hiroshi Shimada、Ken-ichiro Takamiya、Hiroyuki Ohta、Jacques Joyard

  DOI：10.1073/pnas.181331498

  日期：2001.9.11

  In Arabidopsis , monogalactosyldiacylglycerol (MGDG) is synthesized by a multigenic family of MGDG synthases consisting of two types of enzymes differing in their N-terminal portion: type A (atMGD1) and type B (atMGD2 and atMGD3). The present paper compares type B isoforms with the enzymes of type A that are known to sit in the inner membrane of plastid envelope. The occurrence of types A and B in 16:3 and 18:3 plants shows that both types are not specialized isoforms for the prokaryotic and eukaryotic glycerolipid biosynthetic pathways. Type A atMGD1 gene is abundantly expressed in green tissues and along plant development and encodes the most active enzyme. Its mature polypeptide is immunodetected in the envelope of chloroplasts from Arabidopsis leaves after cleavage of its transit peptide. atMGD1 is therefore likely devoted to the massive production of MGDG required to expand the inner envelope membrane and build up the thylakoids network. Transient expression of green fluorescent protein fusions in Arabidopsis leaves and in vitro import experiments show that type B precursors are targeted to plastids, owing to a different mechanism. Noncanonical addressing peptides, whose processing could not be assessed, are involved in the targeting of type B precursors, possibly to the outer envelope membrane where they might contribute to membrane expansion. Expression of type B enzymes was higher in nongreen tissues, i.e., in inflorescence ( atMGD2 ) and roots ( atMGD3 ), where they conceivably influence the eukaryotic structure prominence in MGDG. In addition, their expression of type B enzymes is enhanced under phosphate deprivation.

  在拟南芥中，单半乳糖二酰基甘油（MGDG）由由多基因家族的MGDG合成酶合成，由两种不同的酶组成，其N-末端不同：A型（atMGD1）和B型（atMGD2和atMGD3）。本文比较了B型同工酶与已知坐落在质体包膜内膜的A型酶。16：3和18：3植物中A和B型的出现表明，两种类型并不是原核和真核甘油脂生物合成途径的专门同工酶。atMGD1基因在绿色组织和植物发育过程中丰富表达，并编码最活跃的酶。其成熟多肽在转运肽剪切后在拟南芥叶绿体的包膜中被免疫检测到。因此，atMGD1可能专门用于大量生产所需的MGDG，以扩展内包膜膜并建立类囊体网络。在拟南芥叶片中绿色荧光蛋白融合的瞬时表达和体外进口实验表明，B型前体由于不同的机制被定位到质体中。非规范寻址肽参与了B型前体的定位，其加工无法评估，可能定位于外包膜膜，从而有助于膜的扩张。B型酶的表达在非绿色组织，即花序（atMGD2）和根（atMGD3）中更高，它们可能影响MGDG中真核结构的突出性。此外，在缺磷条件下，B型酶的表达得到增强。
• WO2008/124729
  申请人：——

  公开号：——

  公开（公告）日：——
• Bunting M.; Tang W.; Zimmerman G.A., J Biol Chem, 1996, 0021-9258, 10230-6
  作者：Bunting M.、Tang W.、Zimmerman G.A.、McIntyre T.M.、Prescott S.M.

  DOI：——

  日期：——
• A Cardiolipin from <i>Muribaculum intestinale</i> Induces Antigen-Specific Cytokine Responses
  作者：Sunghee Bang、Yern-Hyerk Shin、Xiao Ma、Sung-Moo Park、Daniel B. Graham、Ramnik J. Xavier、Jon Clardy

  DOI：10.1021/jacs.3c09734

  日期：2023.11.1