1,3-di-O-benzoyl-myo-inositol | 162062-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-di-O-benzoyl-myo-inositol
• 英文别名: myo-inositol 1,3-dibenzoate
• CAS: 162062-52-4
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: FULZFGPWFILVPE-SAADCXDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133.52
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  二乙基亚磷酰氯 、 1,3-di-O-benzoyl-myo-inositol 在 sodium phosphate buffer pH 7 、 双氧水 、 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  Synthesis of all possible regioisomers of myo-inositol tetrakisphosphates

  摘要：

  以肌醇为原料，通过其二苯甲酸酯衍生物（IBz2）作为关键中间体，合成了 IP4 的所有可能的九种区域异构体，其中一些被认为是细胞信号传递中的第二信使；碱催化 I(1,4) Bz2 及其衍生物的异构化，然后通过适当的分离程序，有效地提供了 IBz2 的所有九种区域异构体。

  DOI：

  10.1039/c39950000011
• 作为产物：
  描述：

  2,4,6-Tris(benzyloxy)-1,3,5-cyclohexanetriol 在 palladium dihydroxide 氢气 作用下， 以 吡啶 为溶剂， 生成 1,3-di-O-benzoyl-myo-inositol
  参考文献：
  名称：

  Syntheses of myo-inositol-1,2,3,5- and -2,4,5,6-tetrakisphosphates, unusual inhibitors of myo-inositol-1,4,5-trisphosphate 3-kinase

  摘要：

  D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P-3], a calcium mobilizing second messenger, is converted to D-I(1,3,4,5)P-4 by D-I(1,4,5)P-3-3-kinase. Efficient syntheses of I(1,2,3,5)P-4 (2) and I(2,4,5,6)P-4 (3), novel 3-kinase inhibitors, are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10061-0

文献信息

• One-Step Regioselective Functionalization of myo-Inositol by Dissolution Strategy
  作者：Yutaka Watanabe、Satoe Yamauchi、Minoru Hayashi

  DOI：10.1055/s-0029-1217809

  日期：2009.9

  Functionalizations of hydroxy groups of myo-inositol were usually nonselective due to its poor solubility. By dissolving myo-inositol in DMSO or LiCl-N,N-dimethylacetamide, we have achieved regioselective acylation, silylation, sulfonylation, phosphinylation to give the corresponding 1,3-di-O-substituted products in good yields.

  由于肌醇的溶解性差，羟基的功能化通常是非选择性的。我们通过将肌醇溶解在DMSO或氯化锂- N,N-二甲基乙酰胺中，实现了区域选择性的酰化、硅化、磺酰化和磷酸化，获得了相应的1,3-二-O-取代产品，并取得了较好的产率。
• Base-catalysed acyl migrations in myo-inositol dibenzoates
  作者：Sung-Kee Chung、Young-Tae Chang

  DOI：10.1039/c39950000013

  日期：——

  Base-catalysed isomerizations of readily available I(1,4) Bz2 and its derivatives efficiently provided all nine regioisomers of IBz2 and the kinetic behaviour of the benzoyl-migration has been studied.

  通过碱催化 I(1,4) Bz2 及其衍生物的异构化，有效地提供了 IBz2 的全部九种区域异构体，并对苯甲酰基迁移的动力学行为进行了研究。
• <scp>HIV</scp>‐1 Gag <scp>MA</scp> domain binds to cardiolipin in a binding mode distinct from virus assemble mediator <scp>PI</scp>(4,5)<scp>P₂</scp>
  作者：Hiroshi Tateishi、Takuma Chinen、Ryota Fukuda、Mohamed O. Radwan、Kazunori Shimagaki、Ryoko Koga、Takashi Masuda、Yoshinari Okamoto、Arisa Sakamoto、Shogo Misumi、Masami Otsuka、Mikako Fujita、Kensaku Anraku

  DOI：10.1111/cbdd.14401

  日期：2024.1

  The human immunodeficiency virus type 1 (HIV‐1) Gag protein is responsible for facilitating HIV‐1 virion assembly and budding. Our study demonstrates that cardiolipin (CL), a component found in the inner mitochondrial membrane, exhibits the highest binding affinity to the N‐terminal MA domain of the HIV‐1 Gag protein within the lipid group of host cells. To assess this binding interaction, we synthesized short acyl chain derivatives of CL and employed surface plasmon resonance (SPR) analysis to determine the dissociation constants (Kd) for CL and the MA domain. Simultaneously, we examined the Kd of D‐myo‐phosphatidylinositol 4,5‐bisphosphate (PI(4,5)P₂) derivatives, known to play a crucial role in virion formation. Among all the derivatives, Tetra‐C₇‐CL exhibited the lowest Kd value (Kd = 30.8 ± 6.9 μM) for MA binding on the CL analog‐immobilized sensorchip, indicating a higher affinity. Similarly, the Kd value of Di‐C₇‐PIP2 (Kd = 36.6 ± 4.7 μM) was the lowest on the PI(4,5)P₂ analog‐immobilized sensorchip. Thus, Tetra‐C₇‐CL binds to the MA domain using a distinct binding mode while displaying a comparable binding affinity to Di‐C₇‐PIP2. This discovery holds significant implications for comprehending the virological importance of CL–MA domain binding, such as its subcellular distribution, including mitochondrial translocation, and involvement in viral particle formation in concert with PI(4,5)P₂. Furthermore, this study has the potential to contribute to the development of drugs in the future.

  摘要 人类免疫缺陷病毒 1 型（HIV-1）Gag 蛋白负责促进 HIV-1 病毒的组装和出芽。我们的研究表明，线粒体内膜中的一种成分--心磷脂（CL）与宿主细胞脂质组中 HIV-1 Gag 蛋白 N 端 MA 结构域的结合亲和力最高。为了评估这种结合相互作用，我们合成了 CL 的短酰基链衍生物，并利用表面等离子体共振（SPR）分析确定了 CL 与 MA 结构域的解离常数（Kd）。同时，我们还检测了D-肌磷脂酰肌醇-4,5-二磷酸（PI(4,5)P2）衍生物的Kd，众所周知，PI(4,5)P2在病毒形成过程中起着至关重要的作用。在所有衍生物中，Tetra-C7-CL 与 MA 在 CL 类似物固定的传感器芯片上结合的 Kd 值最低（Kd = 30.8 ± 6.9 μM），表明其亲和力较高。同样，在 PI(4,5)P2 类似物固定的传感器芯片上，Di-C7-PIP2 的 Kd 值（Kd = 36.6 ± 4.7 μM）最低。因此，Tetra-C7-CL 采用一种独特的结合模式与 MA 结构域结合，同时显示出与 Di-C7-PIP2 相当的结合亲和力。这一发现对理解 CL-MA 结构域结合在病毒学上的重要性具有重要意义，例如它的亚细胞分布，包括线粒体转运，以及与 PI(4,5)P2 共同参与病毒颗粒的形成。此外，这项研究还有可能促进未来药物的开发。
• Regioselective functionalization of unprotected myo-inositol by electrophilic substitution
  作者：Yutaka Watanabe、Tsuyoshi Uemura、Satoe Yamauchi、Kousei Tomita、Takafumi Saeki、Ryousuke Ishida、Minoru Hayashi

  DOI：10.1016/j.tet.2013.03.109

  日期：2013.6

  Unprotected myo-inositol was treated with various electrophiles, such as aroyl chlorides, tosyl chloride and tert-butyldiphenylsilyl chloride in a solution of LiCl/DMA or DMSO to afford regioselectively l,3-di-O-substituted or racemic 1-O-substituted derivatives, depending on a quantity of reagents and reaction time. alpha-Unbranched alkanoic acid anhydrides in LiCl/DMA in the presence of triethylamine were suitable for acylation of myo-inositol, in contrast to the fact that acylation using alkanoyl chlorides in aprotic polar solvents generally does not proceed well due to decomposition of the reagents by the reaction with the solvents. (C) 2013 Elsevier Ltd. All rights reserved.