L-(E)-4,5-dehydroarginine | 1272029-44-3

• 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
• 英文名称: L-(E)-4,5-dehydroarginine
• 英文别名: (E,2S)-2-amino-5-(diaminomethylideneamino)pent-4-enoic acid
• CAS: 1272029-44-3
• 化学式: C₆H₁₂N₄O₂
• 分子量: 172.187
• InChiKey: FVSQXMGZDMFDEJ-REJIZHKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.21
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125.22
• 氢给体数：
  5.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  丹酰氯 、 L-(E)-4,5-dehydroarginine 在 lithium carbonate 作用下， 反应 1.0h， 以27%的产率得到N-dansyl-L-(E)-4,5-dehydroarginine
  参考文献：
  名称：

  Core Assembly Mechanism of Quinocarcin/SF-1739: Bimodular Complex Nonribosomal Peptide Synthetases for Sequential Mannich-type Reactions

  摘要：

  Quinocarcin and SF-1739, potent antitumor antibiotics, share a common tetracyclic tetrahydroisoquinoline (THIQ)-pyrrolidine core scaffold. Herein, we describe the identification of their biosynthetic gene clusters and biochemical analysis of Qcn18/ Cya18 generating the previously unidentified extender unit dehydroarginine, which is a component of the pyrrolidine ring. ATP-inorganic pyrophosphate exchange experiments with five nonribosomal peptide synthetases (NRPSs) enabled us to identify their substrates. On the basis of these data, we propose that a biosynthetic pathway comprising a threecomponent NRPS/MbtH family protein complex, Qcn16/17/19, plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold involving sequential Pictet-Spengler and intramolecular Mannich reactions. Furthermore, data derived from gene inactivation experiments led us to propose late-modification steps of quinocarcin.

  DOI：

  10.1016/j.chembiol.2013.10.011
• 作为产物：
  描述：

  L-精氨酸 在 alpha-酮戊二酸 、 L-1,4-二硫代苏糖醇 、 non-heme iron oxygenase Cya₁₈ 、 iron(II) sulfate 、 维生素 C 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 L-(E)-4,5-dehydroarginine
  参考文献：
  名称：

  Core Assembly Mechanism of Quinocarcin/SF-1739: Bimodular Complex Nonribosomal Peptide Synthetases for Sequential Mannich-type Reactions

  摘要：

  Quinocarcin and SF-1739, potent antitumor antibiotics, share a common tetracyclic tetrahydroisoquinoline (THIQ)-pyrrolidine core scaffold. Herein, we describe the identification of their biosynthetic gene clusters and biochemical analysis of Qcn18/ Cya18 generating the previously unidentified extender unit dehydroarginine, which is a component of the pyrrolidine ring. ATP-inorganic pyrophosphate exchange experiments with five nonribosomal peptide synthetases (NRPSs) enabled us to identify their substrates. On the basis of these data, we propose that a biosynthetic pathway comprising a threecomponent NRPS/MbtH family protein complex, Qcn16/17/19, plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold involving sequential Pictet-Spengler and intramolecular Mannich reactions. Furthermore, data derived from gene inactivation experiments led us to propose late-modification steps of quinocarcin.

  DOI：

  10.1016/j.chembiol.2013.10.011