CMP-5'-3APn | 1346431-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: CMP-5'-3APn
• 英文别名: CMP-5'-3-aminopropylphosphonate；[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-(3-aminopropyl)phosphinic acid
• CAS: 1346431-49-9
• 化学式: C₁₂H₂₂N₄O₁₀P₂
• 分子量: 444.275
• InChiKey: OGKREJFVUHDHTP-QCNRFFRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  228
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  CMP-5'-3APn 、 胞苷-5’-三磷酸 、 乙酰辅酶A 在 His₆-FrbF enzyme 、 His₆-FrbG enzyme 、 His₆-FrbH enzyme 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 生成 CMP-5'-N-acetyl-3-aminopropylphosphonate 、 CMP-5'-FR-900098
  参考文献：
  名称：

  Deciphering the Late Biosynthetic Steps of Antimalarial Compound FR-900098

  摘要：

  FR-900098 is a potent chemotherapeutic agent for the treatment of malaria. Here we report the heterologous production of this compound in Escherichia coli by reconstructing the entire biosynthetic pathway using a three-plasmid system. Based on this system, whole-cell feeding assays in combination with in vitro enzymatic activity assays reveal an unusual functional role of nucleotide conjugation and lead to the complete elucidation of the previously unassigned late biosynthetic steps. These studies also suggest a biosynthetic route to a second phosphonate antibiotic, FR-33289. A thorough understanding of the FR-900098 biosynthetic pathway now opens possibilities for metabolic: engineering in E. coli to increase production of the antimalarial antibiotic and combinatorial biosynthesis to generate novel derivatives of FR-900098.

  DOI：

  10.1016/j.chembiol.2009.12.009
• 作为产物：
  描述：

  2-氨基-4-膦酰丁酸 、 胞苷-5’-三磷酸 在 His₆-FrbH enzyme 、 magnesium chloride 作用下， 反应 2.0h， 生成 CMP-5'-3APn 、 CMP-5'-2APn 、 5'-胞苷酸 、 胞苷-5’-二磷酸
  参考文献：
  名称：

  Deciphering the Late Biosynthetic Steps of Antimalarial Compound FR-900098

  摘要：

  FR-900098 is a potent chemotherapeutic agent for the treatment of malaria. Here we report the heterologous production of this compound in Escherichia coli by reconstructing the entire biosynthetic pathway using a three-plasmid system. Based on this system, whole-cell feeding assays in combination with in vitro enzymatic activity assays reveal an unusual functional role of nucleotide conjugation and lead to the complete elucidation of the previously unassigned late biosynthetic steps. These studies also suggest a biosynthetic route to a second phosphonate antibiotic, FR-33289. A thorough understanding of the FR-900098 biosynthetic pathway now opens possibilities for metabolic: engineering in E. coli to increase production of the antimalarial antibiotic and combinatorial biosynthesis to generate novel derivatives of FR-900098.

  DOI：

  10.1016/j.chembiol.2009.12.009

文献信息

• Deciphering the Late Biosynthetic Steps of Antimalarial Compound FR-900098
  作者：Tyler W. Johannes、Matthew A. DeSieno、Benjamin M. Griffin、Paul M. Thomas、Neil L. Kelleher、William W. Metcalf、Huimin Zhao

  DOI：10.1016/j.chembiol.2009.12.009

  日期：2010.1

  FR-900098 is a potent chemotherapeutic agent for the treatment of malaria. Here we report the heterologous production of this compound in Escherichia coli by reconstructing the entire biosynthetic pathway using a three-plasmid system. Based on this system, whole-cell feeding assays in combination with in vitro enzymatic activity assays reveal an unusual functional role of nucleotide conjugation and lead to the complete elucidation of the previously unassigned late biosynthetic steps. These studies also suggest a biosynthetic route to a second phosphonate antibiotic, FR-33289. A thorough understanding of the FR-900098 biosynthetic pathway now opens possibilities for metabolic: engineering in E. coli to increase production of the antimalarial antibiotic and combinatorial biosynthesis to generate novel derivatives of FR-900098.