Hexaacetyl-epi-inosamin-6 | 18779-77-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Hexaacetyl-epi-inosamin-6
• 英文别名: scyllo-inosamine hexaacetate；penta-O-acetyl-6-acetylamino-6-deoxy-epi-inositol
• CAS: 18779-77-6
• 化学式: C₁₈H₂₅NO₁₁
• 分子量: 431.397
• InChiKey: HUIJQCXRTYJHCQ-NSGFAUEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.84
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  160.6
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Hexaacetyl-epi-inosamin-6 在 氨 作用下， 以 甲醇 为溶剂， 生成 N-Acetyl-epi-inosamin-6
  参考文献：
  名称：

  氨基环醇。十三、链霉胺的合成研究

  摘要：

  从表肌醇开始，两种新的肌胺：epi-1 和epi-6，以及两种肌苷胺：myo-4、6 和链霉胺，已经通过用叠氮化物离子取代磺酸盐基团来制备。核磁共振波谱确定了产品的构型。

  DOI：

  10.1246/bcsj.40.1925
• 作为产物：
  描述：

  scyllo-inosamine hydrochloride 、 乙酸酐 在 吡啶 作用下， 反应 48.0h， 生成 Hexaacetyl-epi-inosamin-6
  参考文献：
  名称：

  Chemical synthesis of scyllo-inosamine and catabolism studies in Sinorhizobium meliloti

  摘要：

  Rhizopines such as scyllo-inosamine (SIA) and L-3-O-methyl-scyllo-inosamine (3-O-MSI) play an intricate role as nutritional mediators during the establishment of the symbiotic relationship between legumes and rhizobia. The mechanism of action is not well understood. One challenge is the availability of rhizopines, which occur in only minute amounts in plant nodules. We herewith report an efficient synthesis of scyllo-inosamine and its biochemical activity in specific bacteria. SIA was prepared in 7 steps and 32% overall yield from readily available myo-inositol. The chemically synthesized SIA was tested to determine whether it can serve as sole carbon and nitrogen source for Sinorhizobium meliloti wild-type strain L5-30 and for strains carrying mutations in the rhizopine degradation (moc) genes. The analysis of the phenotype of the mutant strains revealed that the moc genes previously shown to be essential for the breakdown of the rhizopines isolated from root nodules are also essential for the utilization of the chemically synthesized SIA. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.06.040