9-Dodecenoic acid, DMOX derivative

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 9-Dodecenoic acid, DMOX derivative
• 英文别名: 4,4-dimethyl-2-[(Z)-undec-8-enyl]-5H-1,3-oxazole
• 化学式: C₁₆H₂₉NO
• 分子量: 251.41
• InChiKey: YOAQXFRSXOZXQL-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-2-甲基-1-丙醇 、 variochelin D 在 盐酸 作用下， 以 水 为溶剂， 生成 9-Dodecenoic acid, DMOX derivative
  参考文献：
  名称：

  New variochelins from soil-isolated Variovorax sp. H002

  摘要：

  The soil bacterial genus Variovorax produce distinct photoreactive siderophores that may play a crucial role in the iron cycle within the rhizosphere. This study focused on exploring the natural products of the soil-isolated Variovorax sp. H002, leading to the isolation of variochelins A–E (1–5), a series of lipohexapeptide siderophores. NMR and MS/MS analyses revealed that these siderophores share a common core structure – a linear hexapeptide with β-hydroxyaspartate and hydroxamate functional groups, serving in iron-binding coordination. Three new variochelins C–E (3–5) were characterized by varied fatty acyl groups at their N-termini; notably, 4 and 5 represent the first variochelins with N-terminal unsaturated fatty acyl groups. Furthermore, the variochelin biosynthetic gene cluster was identified through draft genome sequencing and gene knockout experiments. Compounds 1–5 exhibited antimicrobial activities against Gram-negative bacteria, including several soil-isolated plant pathogens.

  DOI：

  10.3762/bjoc.20.63

文献信息

• New variochelins from soil-isolated <i>Variovorax</i> sp. H002
  作者：Jabal Rahmat Haedar、Aya Yoshimura、Toshiyuki Wakimoto

  DOI：10.3762/bjoc.20.63

  日期：——

  The soil bacterial genus Variovorax produce distinct photoreactive siderophores that may play a crucial role in the iron cycle within the rhizosphere. This study focused on exploring the natural products of the soil-isolated Variovorax sp. H002, leading to the isolation of variochelins A–E (1–5), a series of lipohexapeptide siderophores. NMR and MS/MS analyses revealed that these siderophores share a common core structure – a linear hexapeptide with β-hydroxyaspartate and hydroxamate functional groups, serving in iron-binding coordination. Three new variochelins C–E (3–5) were characterized by varied fatty acyl groups at their N-termini; notably, 4 and 5 represent the first variochelins with N-terminal unsaturated fatty acyl groups. Furthermore, the variochelin biosynthetic gene cluster was identified through draft genome sequencing and gene knockout experiments. Compounds 1–5 exhibited antimicrobial activities against Gram-negative bacteria, including several soil-isolated plant pathogens.