LM-NS01A-Me | 1314639-76-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: LM-NS01A-Me
• 英文别名: methyl (2R)-2-[(2S,3R,4S,5R,7R,9S,10S,11R,12S,13R)-4-acetyloxy-12-[(2R,4R,5R,6S)-5-acetyloxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-10-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-6,14-dioxo-oxacyclotetradec-2-yl]propanoate
• CAS: 1314639-76-3
• 化学式: C₄₂H₇₀O₁₆
• 分子量: 831.008
• InChiKey: XFFJHVRZSNFEKU-MDGZKKNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  58
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 LM-NS01A 、 LM-NS01B 以 乙醚 为溶剂， 反应 1.0h， 以4.5 mg的产率得到LM-NS01A-Me
  参考文献：
  名称：

  Isolation, structural elucidation, and biosynthesis of 15-norlankamycin derivatives produced by a type-II thioesterase disruptant of Streptomyces rochei

  摘要：

  Lankamycin, a 14-membered macrolide antibiotic, contains a 3-hydroxy-2-butyl side chain at C-13. To analyze the function of lkmE, which encodes type-II thioesterase in the lankamycin cluster, we carried out a gene disruption experiment. Disruption of lkmE resulted in a 70% decrease of lankamycin production concomitant with an accumulation of novel lankamycin derivatives (LM-NS01A and LM-NS01B), in which the C-13 side chain is replaced by a 1-carboxyethyl group. The biosynthetic origin of 1-carboxyethyl group was confirmed by incorporation of deuterium in [3-(2)H]3-methyl-2-oxobutyrate into the C-14 position. These results indicate that the biosynthesis of LM-NS01A and LM-NS01B starts from isobutyryl CoA in place of (S)-2-methylbutyryl CoA and LkmE removes the aberrantly loaded starter unit and restores lankamycin production. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.047