19-dechloro-4,5-deepoxy-N-demethyl-20-N-ureidoansamitocin P-3 | 1452403-05-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 19-dechloro-4,5-deepoxy-N-demethyl-20-N-ureidoansamitocin P-3
• 英文别名: [(3E,5E,7R,8S,12S,13S,14E,16S)-22-(carbamoylamino)-8-hydroxy-7-methoxy-3,13,15-trimethyl-10,18-dioxo-11-oxa-9,19-diazatricyclo[18.3.1.18,12]pentacosa-1(24),3,5,14,20,22-hexaen-16-yl] 2-methylpropanoate
• CAS: 1452403-05-2
• 化学式: C₃₁H₄₂N₄O₈
• 分子量: 598.696
• InChiKey: NYHAUWRNXPGEDZ-GBVXFHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  43
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  178
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-amino-5-azidobenzoic acid 在 mutant strain of Actinosynnema pretiosum HGF₀₇₃ 作用下， 以 水 、 二甲基亚砜 为溶剂， 以1.2 mg的产率得到20-amino-19-dechloroansamitocin P-3
  参考文献：
  名称：

  Bioreduction of Aryl Azides during Mutasynthesis of New Ansamitocins

  摘要：

  Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic acid, unexpectedly yielded anilino ansamitocins instead of the expected azido derivatives. This is the first example of the bioreduction of organic azides. The unique nature of these results was demonstrated when 3-azido-5-amino-benzoic acid was fed to the corresponding AHBA blocked mutant of Streptomyces hygroscopicus, the geldanamycin producer. This mutasynthetic experiment yielded the fully processed azido derivative of geldanamycin.

  DOI：

  10.1021/ol401989e