2-[[[(3R,5R)-3-氨基-6-[[(2S)-2-氨基-4-甲基戊酰基]氨基]-5-羟基己烷酰基]氨基]-甲基氨基]乙酸 | 35663-84-4

• 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
• 中文名称: 2-[[[(3R,5R)-3-氨基-6-[[(2S)-2-氨基-4-甲基戊酰基]氨基]-5-羟基己烷酰基]氨基]-甲基氨基]乙酸
• 英文名称: Leucylnegamycin
• 英文别名: 2-[[[(3R,5R)-3-amino-6-[[(2S)-2-amino-4-methylpentanoyl]amino]-5-hydroxyhexanoyl]amino]-methylamino]acetic acid
• CAS: 35663-84-4
• 化学式: C₁₅H₃₁N₅O₅
• 分子量: 361.442
• InChiKey: BRLOZZKKEWGIEL-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  171
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3R,5R)-6-Azido-3-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid pentafluorophenyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 2-[[[(3R,5R)-3-氨基-6-[[(2S)-2-氨基-4-甲基戊酰基]氨基]-5-羟基己烷酰基]氨基]-甲基氨基]乙酸
  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

文献信息

• N- and C-terminal modifications of negamycin
  作者：B Raju、Kathleen Mortell、Sampathkumar Anandan、Hardwin O'Dowd、Hongwu Gao、Marcela Gomez、Corinne Hackbarth、Charlotte Wu、Wen Wang、Zhengyu Yuan、Richard White、Joaquim Trias、Dinesh V Patel

  DOI：10.1016/s0960-894x(03)00393-7

  日期：2003.7

  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.