Pseudotrienic acid B | 868592-46-5

• 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: Pseudotrienic acid B
• 英文别名: (+)-(2E,4E,6E)-9-{(2S,3R)-3-hydroxy-4-[(3E,5E)-7-hydroxy-4-methyltetradeca-3,5-dienamido]-2-methylbutanamido}nona-2,4,6-trienoic acid；(2E,4E,6E)-9-[[(2S,3R)-3-hydroxy-4-[[(3E,5E)-7-hydroxy-4-methyltetradeca-3,5-dienoyl]amino]-2-methylbutanoyl]amino]nona-2,4,6-trienoic acid
• CAS: 868592-46-5
• 化学式: C₂₉H₄₆N₂O₆
• 分子量: 518.694
• InChiKey: KUBFEPFJIGSSKC-DXIDGMHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  136
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Pseudotrienic acid B 在 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 生成 (7R,8S,13E,15E,17E)-2-[(2E,4E)-dodeca-2,4-dien-2-yl]-7-hydroxy-8-methyl-1-oxa-5,10-diazacyclononadeca-13,15,17-triene-4,9,19-trione
  参考文献：
  名称：

  Pseudotrienic Acids A and B, Two Bioactive Metabolites from Pseudomonas sp. MF381-IODS

  摘要：

  Bioassay-guided fractionation of the liquid culture broth of Pseudomonas sp. MF381-IODS yielded two new antimicrobial substances, identified as (2E,4E,6E)-9-[((2S,3R)-3-hydroxy-4-{[(3E,5E,7RS)-7-hydroxy-4-methylhexadeca-3,5-dienoyl]amino}-2-methylbutanoyl)amino]nona-2,4,6-trienoic acid and the tetradeca equivalent, named pseudotrienic acids A (1) and B (2), respectively. The compounds are prone to lactone formation, and their structures suggest them to be derived from ring opening of a macrolide. Pseudotrienic acids A and B inhibited growth of Staphylococcus aureus (MIC 70 mu g/mL) and Pseudomonas syringae pv. syringae (MIC 70 mu g/mL). Two known antimicrobial compounds, the polyketide 2,3-deepoxy-2,3-didehydrorhizoxin (3) and the tryptophan-derived pyrrolnitrin (4), were also identified.

  DOI：

  10.1021/np050243a
• 作为产物：
  描述：

  (E)-4-tributylstannylpent-3-en-1-ol 在 双(乙腈)氯化钯(II) N-甲基吗啉 、 chromium(VI) oxide 、 lithium hydroxide 、 硫酸 、 碘 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 36.5h， 生成 Pseudotrienic acid B
  参考文献：
  名称：

  假三烯酸B的全合成：假单胞菌属种的生物活性代谢产物。MF 381-IODS。

  摘要：

  DOI：

  10.1002/anie.200601114

文献信息

• Synthesis of Two Bioactive Natural Products: FR252921 and Pseudotrienic Acid B
  作者：Dominique Amans、Véronique Bellosta、Janine Cossy

  DOI：10.1002/chem.200802649

  日期：2009.3.23

  Jackpot: Two for one! Concise and highly convergent syntheses of the immunosuppressive agent FR252921 and the related antimicrobial natural product pseudotrienic acid B were achieved from one common intermediate by using optically active titanium complexes to control the configuration of the stereogenic centers, a highly stereo‐ and regioselective cross‐metathesis to generate the triene moieties, and

  头奖：二合一！免疫抑制剂FR252921和相关的抗菌天然产物假三烯酸B的简明和高度融合合成是通过使用旋光性钛络合物控制立体生成中心的构型，高度立体和区域选择性交叉复分解而从一个常见的中间体实现的生成三烯部分，和Stille交叉耦合以安装二烯单元。
• Pseudotrienic Acids A and B, Two Bioactive Metabolites from <i>Pseudomonas</i> sp. MF381-IODS
  作者：Anton Pohanka、Anders Broberg、Maria Johansson、Lennart Kenne、Jolanta Levenfors

  DOI：10.1021/np050243a

  日期：2005.9.1

  Bioassay-guided fractionation of the liquid culture broth of Pseudomonas sp. MF381-IODS yielded two new antimicrobial substances, identified as (2E,4E,6E)-9-[((2S,3R)-3-hydroxy-4-[(3E,5E,7RS)-7-hydroxy-4-methylhexadeca-3,5-dienoyl]amino}-2-methylbutanoyl)amino]nona-2,4,6-trienoic acid and the tetradeca equivalent, named pseudotrienic acids A (1) and B (2), respectively. The compounds are prone to lactone formation, and their structures suggest them to be derived from ring opening of a macrolide. Pseudotrienic acids A and B inhibited growth of Staphylococcus aureus (MIC 70 mu g/mL) and Pseudomonas syringae pv. syringae (MIC 70 mu g/mL). Two known antimicrobial compounds, the polyketide 2,3-deepoxy-2,3-didehydrorhizoxin (3) and the tryptophan-derived pyrrolnitrin (4), were also identified.
• Total Synthesis of Pseudotrienic Acid B: A Bioactive Metabolite fromPseudomonas sp. MF 381-IODS
  作者：Dominique Amans、Véronique Bellosta、Janine Cossy

  DOI：10.1002/anie.200601114

  日期：2006.9.4