8-deoxy-16-descarboxyl-16-methyl-amphoteronolide B | 1228440-85-4

• 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: 8-deoxy-16-descarboxyl-16-methyl-amphoteronolide B
• 英文别名: (1R,3S,5S,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-1,3,5,9,11,17,33,37-octahydroxy-15,16,18,36-tetramethyl-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaen-13-one
• CAS: 1228440-85-4
• 化学式: C₄₁H₆₄O₁₁
• 分子量: 732.953
• InChiKey: GCXLOVOVIUYGGR-WFMXRCILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  52
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  8-deoxy-16-descarboxyl-16-methyl-amphoteronolide B 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以325 mg的产率得到(3R,5R,9S,11S,15R,17S,19S,35S)-octabenzoyloxy-13-oxo-(16S,34S,36S)-trimethyl-(20E,22E,24E,26E,28E,30E,32E)-octatriacontaheptaeno-(37S)-lactone
  参考文献：
  名称：

  Isolation and characterisation of amphotericin B analogues and truncated polyketide intermediates produced by genetic engineering of Streptomyces nodosus

  摘要：

  Amphotericin B is a powerful but toxic drug used against fungal infections and leishmaniases. These diseases would be treated more effectively if non-toxic amphotericin derivatives could be produced on a large scale at low cost. Genetic manipulation of the amphotericin B producer, Streptomyces nodosus, has previously led to the detection and partial characterisation of 8-deoxyamphotericin B, 16-descarboxyl-16-methyl-amphotericin B, 15-deoxy-16-descarboxyl-16-methyl-15-oxo-amphotericin B, 7-oxo-amphotericin B and pentaene analogues. Here we report improved production and purification protocols that have allowed detailed chemical analyses of these compounds. The polyketide synthase product 8-deoxy-16-descarboxyl-16-methyl-amphoteronolide B was identified for the first time. In addition, the ketoreductase 10 domain of the polyketide synthase was specifically inactivated by targeted gene replacement. The resulting mutants produced truncated polyketide intermediates as linear polyenyl-pyrones.

  DOI：

  10.1039/b922074g