terfestatin A | 804556-26-1

• 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: terfestatin A
• 英文别名: (2S,3R,4S,5S,6R)-2-(2,4-dihydroxy-3,6-diphenylphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 804556-26-1
• 化学式: C₂₄H₂₄O₈
• 分子量: 440.45
• InChiKey: UTRHHGVQLUCOIT-NZXWXYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  terfestatin A 在 盐酸 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 27.0h， 生成 2',3',5'-triacetoxy-p-terphenyl
  参考文献：
  名称：

  The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.

  摘要：

  Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestatin A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl beta-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.055
• 作为产物：
  描述：

  3',5'-dibenzyloxy-2'-hydroxy-p-terphenyl 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 caesium carbonate 作用下， 以 甲醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 49.0h， 生成 terfestatin A
  参考文献：
  名称：

  The isolation, structural determination, and total synthesis of terfestatin A, a novel auxin signaling inhibitor from Streptomyces sp.

  摘要：

  Indole 3-acetic acid, a plant hormone auxin, regulates every aspects of plant growth and development. In the screening for specific inhibitors on auxin signaling using the transgenic Arabidopsis plant harboring the auxin-responsive reporter gene, terfestatin A was found to be a novel inhibitor of auxin signaling from the culture of Streptomyces sp. F40. The structure of terfestatin A was determined to be p-terphenyl beta-glucoside on the basis of spectroscopic analyses, chemical degradation, and total synthesis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.055

文献信息

• Total synthesis of terfestatins a and B
  作者：Shun Sugawara、Yasuhiro Meguro、Shuntaro Sato、Masaru Enomoto、Yusuke Ogura、Shigefumi Kuwahara

  DOI：10.1016/j.tetlet.2020.151891

  日期：2020.5

  inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality

  Terfestatin A，一种植物生长素信号转导的特异性抑制剂，已通过五个步骤由一种已知的芳香醛以21％的总收率合成。具有八种有效神经保护活性的terfestatin B的第一个全合成反应，是通过相同的中间体，以相同的芳族醛，以30％的总收率，通过八个步骤完成的。该合成的关键特征是利用原料的醛官能度作为区域选择性O-保护的指导基团和作为掩蔽的羟基。