N-desmethyl 12-keto pretubulysin D | 1258951-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-desmethyl 12-keto pretubulysin D
• 英文别名: (2S,4R)-2-methyl-4-[[2-[(3S)-4-methyl-3-[[(2S,3S)-3-methyl-2-[[(2R)-1-methylpiperidine-2-carbonyl]amino]pentanoyl]amino]-2-oxopentyl]-1,3-thiazole-4-carbonyl]amino]-5-phenylpentanoic acid
• CAS: 1258951-28-8
• 化学式: C₃₅H₅₁N₅O₆S
• 分子量: 669.886
• InChiKey: HGQBQUQITHSXOR-SDSVIOFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氧气 作用下， 反应 192.0h， 以1.3 mg的产率得到N-desmethyl 12-keto pretubulysin D
  参考文献：
  名称：

  Discovery of 23 Natural Tubulysins from Angiococcus disciformis An d48 and Cystobacter SBCb004

  摘要：

  The tubulysins are a family of complex peptides with promising cytotoxic activity against multi-drug-resistant tumors. To date, ten tubulysins have been described from the myxobacterial strains Angiococcus disciformis An d48 and Archangium gephyra Ar 315. We report here a third producing strain, Cystobacter sp. SBCb004. Comparison of the tubulysin biosynthetic gene clusters in SBCb004 and An d48 reveals a conserved architecture, allowing the assignment of cluster boundaries. A SBCb004 strain containing a mutant in the putative cyclodeaminase gene tubZ accumulates pretubulysin A, the proposed first enzyme-free intermediate in the pathway, whose structure we confirm by NMR. We further show, using a combination of feeding studies and structure elucidation by NMR and high-resolution tandem mass spectrometry, that SBCb004 and An d48 together biosynthesize 22 additional tubulysin derivatives. These data reveal the inherently diversity-oriented nature of the tubulysin biosynthetic pathway.

  DOI：

  10.1016/j.chembiol.2010.01.016