(2R,4S)-2-hydroxymethyl-4-[(S)-N-(6-aminohexanoyl)serylamino]-6-methyl-1,2-oxiranylheptane | 214753-97-6

• 分子结构分类: 有机化合物
• 英文名称: (2R,4S)-2-hydroxymethyl-4-[(S)-N-(6-aminohexanoyl)serylamino]-6-methyl-1,2-oxiranylheptane
• CAS: 214753-97-6
• 化学式: C₁₈H₃₃N₃O₆
• 分子量: 387.477
• InChiKey: CYDFXZASBBTCKU-SUNYJGFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.16
• 重原子数：
  27.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  154.28
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-2-hydroxymethyl-4-[(S)-N-(6-aminohexanoyl)serylamino]-6-methyl-1,2-oxiranylheptane 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 反应 8.0h， 以81%的产率得到dihydroeponemycin-biotin
  参考文献：
  名称：

  Eponemycin analogues: syntheses and use as probes of angiogenesis

  摘要：

  Derivatives of the epoxy-beta-aminoketone containing natural product eponemycin have been prepared in order to study the molecular mode of action of this anti-angiogenic compound. Synthesis and use of a biotinylated dihydroeponemycin analogue demonstrated that dihydroeponemycin forms a covalent adduct with at least two intracellular proteins in human endothelial cells. Pretreatment of cells with a five equivalent excess of dihydroeponemycin precluded biotin-dihydroeponemycin binding indicating a specific interaction between natural product and the target proteins. This biotin-dihydroeponemycin derivative will prove useful in the purification and identification of eponemycin receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00089-3
• 作为产物：
  描述：

  N-carbobenzoxy-L-leucinal 在 palladium on activated charcoal 咪唑 、 草酰氯 、 四丁基氟化铵 、 氢气 、 双氧水 、 叔丁基锂 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯甲腈 为溶剂， 反应 43.5h， 生成 (2R,4S)-2-hydroxymethyl-4-[(S)-N-(6-aminohexanoyl)serylamino]-6-methyl-1,2-oxiranylheptane
  参考文献：
  名称：

  Eponemycin analogues: syntheses and use as probes of angiogenesis

  摘要：

  Derivatives of the epoxy-beta-aminoketone containing natural product eponemycin have been prepared in order to study the molecular mode of action of this anti-angiogenic compound. Synthesis and use of a biotinylated dihydroeponemycin analogue demonstrated that dihydroeponemycin forms a covalent adduct with at least two intracellular proteins in human endothelial cells. Pretreatment of cells with a five equivalent excess of dihydroeponemycin precluded biotin-dihydroeponemycin binding indicating a specific interaction between natural product and the target proteins. This biotin-dihydroeponemycin derivative will prove useful in the purification and identification of eponemycin receptors. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00089-3