(4S)-4,5-dihydro-4-hydroxygeldanamycin | 1391855-83-6

• 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: (4S)-4,5-dihydro-4-hydroxygeldanamycin
• 英文别名: (4S)-4,5-Dihydro-4-hydroxygeldanamycin；[(4E,6S,8S,9S,10E,12S,13R,14S,16R)-6,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18-tetraen-9-yl] carbamate
• CAS: 1391855-83-6
• 化学式: C₂₉H₄₂N₂O₁₀
• 分子量: 578.66
• InChiKey: HNYXYDNFRIJYMY-HBDFPOJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  184
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4S)-4,5-dihydro-4-hydroxygeldanamycin 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以3.0 mg的产率得到[(4E,6S,8S,9S,10E,12S,13R,14S,16R)-9-carbamoyloxy-8,14,19-trimethoxy-13-[(2S)-2-methoxy-2-phenylacetyl]oxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18-tetraen-6-yl] (2S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  Identification of 4,5-Dihydro-4-hydroxygeldanamycins As Shunt Products of Geldanamycin Biosynthesis

  摘要：

  Two new geldanamycin (GDM) analogues, (4S)-4,5-dihydro-4-hydroxygeldanamycin (1) and (4R)-4,5-dihydro-4-hydroxygeldanamycin (2), were identified from Streptomyces hygroscopicus 17997. Compounds 1 and 2 were not normal intermediates of GDM biosynthesis but shunt Products of C-4,5 oxidation catalyzed by GdmP, a cytochrome P450 oxidase acting as a desaturase in GDM biosynthesis. Preliminary assays implied that, Compared with GDM, 1 and 2 exhibited decreased cytotoxicity.

  DOI：

  10.1021/np3001738

文献信息

• Identification of 4,5-Dihydro-4-hydroxygeldanamycins As Shunt Products of Geldanamycin Biosynthesis
  作者：Ting Li、Siyang Ni、Changhong Jia、Hongyuan Wang、Guizhi Sun、Linzhuan Wu、Maoluo Gan、Guangzhi Shan、Weiqing He、Ling Lin、Hongxia Zhou、Yiguang Wang

  DOI：10.1021/np3001738

  日期：2012.8.24

  Two new geldanamycin (GDM) analogues, (4S)-4,5-dihydro-4-hydroxygeldanamycin (1) and (4R)-4,5-dihydro-4-hydroxygeldanamycin (2), were identified from Streptomyces hygroscopicus 17997. Compounds 1 and 2 were not normal intermediates of GDM biosynthesis but shunt Products of C-4,5 oxidation catalyzed by GdmP, a cytochrome P450 oxidase acting as a desaturase in GDM biosynthesis. Preliminary assays implied that, Compared with GDM, 1 and 2 exhibited decreased cytotoxicity.