<13CO15NH2>-6-methoxyanthranilamide | 136247-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: <13CO15NH2>-6-methoxyanthranilamide
• 英文别名: 2-amino-6-methoxy(15N)benzamide
• CAS: 136247-98-8
• 化学式: C₈H₁₀N₂O₂
• 分子量: 168.162
• InChiKey: AQAHTARDEJNYPN-GAWGKFCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <13CO15NH2>-6-methoxyanthranilamide 在 lithium methanethiolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以61.5%的产率得到<13CO15NH2>-6-hydroxyanthranilamide
  参考文献：
  名称：

  Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide

  摘要：

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.

  DOI：

  10.1021/jo00023a036
• 作为产物：
  描述：

  <13CO15NH2>-N-(tert-butoxycarbonyl)-6-methoxyanthranilamide 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以94.7%的产率得到<13CO15NH2>-6-methoxyanthranilamide
  参考文献：
  名称：

  Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide

  摘要：

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.

  DOI：

  10.1021/jo00023a036

文献信息

• Studies on nitrogen metabolism using carbon-13 NMR spectroscopy. 6. Biosynthesis of sarubicin A. Synthesis and incorporation of 6-hydroxy[13CO15NH2]anthranilamide
  作者：Steven J. Gould、Rodney L. Eisenberg

  DOI：10.1021/jo00023a036

  日期：1991.11

  We have previously demonstrated that 6-hydroxyanthranilic acid (3) is specifically incorporated into sarubicin A (1) by Streptomyces helicus. 6-Hydroxyanthranilamide (4) has now been synthesized in five steps from m-anisidine in a manner that allowed efficient introduction of isotope labels to prepare [(CONH2)-C-13-N-15]-4a. A new synthesis of 3 from m-anisidine has also been developed. 4a was fed to S. helicus, and a 1.29% incorporation into 1b was obtained. Examination of the C-13 NMR spectrum of 1b revealed predominantly intact incorporation, with a minor amount of 4a (0.13%) first undergoing in vivo hydrolysis to the corresponding acid. Thus, carboxamide formation is the next step in the biosynthesis of 1.