Spermexatin <3,3,3> | 117680-05-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Spermexatin <3,3,3>
• 英文别名: N'-hydroxy-N-[4-[[5-[hydroxy(methyl)amino]-5-oxopentanoyl]-[3-[[5-[hydroxy(methyl)amino]-5-oxopentanoyl]amino]propyl]amino]butyl]-N'-methylpentanediamide
• CAS: 117680-05-4
• 化学式: C₂₅H₄₆N₆O₉
• 分子量: 574.675
• InChiKey: AJBVISCFHIQJGP-UHFFFAOYSA-N

物化性质

• 密度：
  1.240±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  40
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N1,N4,N8-Tris(N-methyl-N-(benzyloxy)glutaramoyl)spermidine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以91%的产率得到Spermexatin <3,3,3>
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013

文献信息

• Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs
  作者：Sushil K. Sharma、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00122a013

  日期：1989.2

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.