[N'-((3R,5R)-6-Amino-3-tert-butoxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazinomethyl]-methyl-phosphinic acid ethyl ester | 604004-03-7

• 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: [N'-((3R,5R)-6-Amino-3-tert-butoxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazinomethyl]-methyl-phosphinic acid ethyl ester
• CAS: 604004-03-7
• 化学式: C₁₆H₃₅N₄O₆P
• 分子量: 410.451
• InChiKey: XJSHDUKVLNLGLL-LXIFRIQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  143.22
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [N'-((3R,5R)-6-Amino-3-tert-butoxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazinomethyl]-methyl-phosphinic acid ethyl ester 在 盐酸 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 [[[(3R,5R)-3,6-diamino-5-hydroxyhexanoyl]amino]-methylamino]methyl-methylphosphinic acid
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7
• 作为产物：
  描述：

  Boc-(R)-3-氨基-5-己烯酸 在 palladium on activated charcoal 吡啶 、 咪唑 、 lithium hydroxide 、 sodium azide 、 氢氟酸 、 氢气 、 碘 、 碳酸氢钠 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 potassium iodide 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.5h， 生成 [N'-((3R,5R)-6-Amino-3-tert-butoxycarbonylamino-5-hydroxy-hexanoyl)-N-methyl-hydrazinomethyl]-methyl-phosphinic acid ethyl ester
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7