(+)-3,4-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol | 139978-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-3,4-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol
• 英文别名: (3aS,4R,5R,6S,7R,7aR)-6,7-bis(prop-2-enoxy)spiro[3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-2,1'-cyclohexane]-4,5-diol
• CAS: 139978-96-4
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: CIMKHRHCKWPGIN-BPXZUEPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-3,4-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol 在 sodium hydride 、 二正丁基氧化锡 、 乙酰氯 、 cesium fluoride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 (1R,2S,3S,4R,5R,6S)-3,4,5-Tris-allyloxy-6-benzyloxy-cyclohexane-1,2-diol
  参考文献：
  名称：

  光学活性肌醇多磷酸盐的有效化学酶学途径

  摘要：

  摘要从两种对映体中以对映体纯的形式制备了1 d-肌醇的1,4,5-tris-，1,3,4-tris-和1,3,4,5-四-磷酸1,2：5,6-二-O-环己叉基-肌醇的对映体。还描述了通过手性中间体通过相应外消旋酯的对映特异性脱酰作用的简便酶制剂。

  DOI：

  10.1016/0008-6215(92)85038-2
• 作为产物：
  描述：

  (+/-)-1,2:5,6-dicyclohexylidene-myo-inositol 在 氢氧化钾 、 potassium phosphate buffer 、 sodium hydride 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.5h， 生成 (+)-3,4-di-O-allyl-1,2-O-cyclohexylidene-myo-inositol
  参考文献：
  名称：

  光学活性肌醇多磷酸盐的有效化学酶学途径

  摘要：

  摘要从两种对映体中以对映体纯的形式制备了1 d-肌醇的1,4,5-tris-，1,3,4-tris-和1,3,4,5-四-磷酸1,2：5,6-二-O-环己叉基-肌醇的对映体。还描述了通过手性中间体通过相应外消旋酯的对映特异性脱酰作用的简便酶制剂。

  DOI：

  10.1016/0008-6215(92)85038-2

文献信息

• Labeling Cell Surface GPIs and GPI-Anchored Proteins through Metabolic Engineering with Artificial Inositol Derivatives
  作者：Lili Lu、Jian Gao、Zhongwu Guo

  DOI：10.1002/anie.201503814

  日期：2015.8.10

  Glycosylphosphatidylinositol (GPI) anchoring of proteins to the cell surface is important for various biological processes, but GPI‐anchored proteins are difficult to study. An effective strategy was developed for the metabolic engineering of cell‐surface GPIs and GPI‐anchored proteins by using inositol derivatives carrying an azido group. The azide‐labeled GPIs and GPI‐anchored proteins were then tagged

  蛋白质将糖基磷脂酰肌醇（GPI）锚定到细胞表面对于各种生物学过程都很重要，但是GPI锚定的蛋白质却很难研究。通过使用带有叠氮基的肌醇衍生物，为细胞表面GPI和GPI固定蛋白的代谢工程开发了一种有效的策略。然后通过点击反应在活细胞上用生物素标记叠氮化物标记的GPI和GPI锚定的蛋白，从而可以用链霉亲和素偶联的染料或其他分子进一步加工。该策略可用于用各种标签标记GPI锚定的蛋白质，以进行生物学研究。
• An efficient route toD-myo-inositol 1,3,4-triphosphate andD-myo-inositol 1,3,4,5-tetrakisphosphate
  作者：Da-Ming Gou、Ching-Shih Chen

  DOI：10.1016/s0040-4039(00)77699-4

  日期：1992.2

  Multigram quantities of the title compounds in their enantiomerically-pure forms have been prepared by employing a chiral precursor which can be obtained via a facile enzymatic process.
• Molecular Recognition at the Phosphatidylinositol 3,4,5-Trisphosphate-Binding Site. Studies Using the Permuted Isomers of Phosphatidylinositol Trisphosphate
  作者：Da-Sheng Wang、Ao-Lin Hsu、Xueqin Song、Chi-Ming Chiou、Ching-Shih Chen

  DOI：10.1021/jo980356h

  日期：1998.8.1

  Permuted isomers of L-alpha-phosphatidyl-D-myo-inositol trisphosphate (PtdInsP(3)), including PtdIns(3,4,5)P-3, PtdIns(3,4,6)P-3, PtdIns(3,5,6)P-3, and PtdIns(4,5,6)P-3, have been synthesized as part of our effort to understand the underlying principles governing ligand selection for Ptdlns(3,4,5)P-3-specific binding proteins. These PtdInsP(3) isomers are examined by using two PtdIns(3,4,5)P-3-dependent functional assays: binding to the C-terminal SH2 domain of the p85 regulatory subunit of PI 3-kinase and platelet aggregation. Our data show that all these isomers bind to the SH2 domain with comparable affinity despite variation in the regioisomeric distribution of phosphate functions. Moreover, all these phospholipids are capable of triggering platelet aggregation with the relative potency of PtdIns(3,4,5)P-3 > PtdIns(3,5,6)P-3 > PtdIns(4,5,6)P-3 > PtdIns(3,4,6)P-3. Evidence suggests that these PtdInsP(3)'s facilitate cell aggregation by activating Ca2+ influx across the plasma membrane. In contrast, other inositol lipids examined including PtdIns(3,4)P-2, PtdIns(4,5)P-2, PtdIns(3)P, and PtdIns(4)P are ineffective in eliciting the aggregation even at much higher concentrations. Taken together, the present data suggest that the charge density on the phosphorylated inositol ring represents a key factor in determining the phosphoinositide binding specificity of target proteins. It is conceivable that the interaction with the PtdIns(3,4,5)P-3-binding motif requires the participation of all three phosphates on the headgroup of PtdIns(3,4,5)P-3. Consequently, other membrane phosphoinositides (e.g., the bis- and monophosphates) become thermodynamically unfavorable for the binding to these PtdIns(3,4,5)P-3 targets.