tumonoic acid I

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: tumonoic acid I
• 英文别名: (2S,3S)-2-[(2R,3S)-2-[(2S)-1-(2,4-dimethyloctanoyl)pyrrolidine-2-carbonyl]oxy-3-methylpentanoyl]oxy-3-methylpentanoic acid
• 化学式: C₂₇H₄₇NO₇
• 分子量: 497.673
• InChiKey: LWUJNFXMOSWRGO-PIKKEMSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tumonoic acid I 在 4-二甲氨基吡啶 、 (S)-(-)- α-甲基苄胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 、 水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 生成 (2R,3S)-2-羟基-3-甲基戊酸
  参考文献：
  名称：

  Natural Products Chemistry and Taxonomy of the Marine Cyanobacterium Blennothrix cantharidosmum

  摘要：

  A Papua New Guinea field collection of the marine cyanobacterium Blennothrix cantharidosmum was investigated for its cytotoxic constituents. Bioassay-guided isolation defined the cytotoxic components as the known compounds lyngbyastatins 1 and 3. However, six new acyl proline derivatives, tumonoic acids D-I, plus the known tumonoic acid A were also isolated. Their planar structures were defined from NMR and MS data, while their stereostructures followed from a series of chiral chromatographies, degradation sequences, and synthetic approaches. The new compounds were tested in all array of assays, but showed only modest antimalarial and inhibition of quorum sensing activities. Nevertheless, these are the first natural products to be reported from this genus. and this inspired a detailed morphologic and 16S rDNA-based phylogenetic analysis of the producing organism.

  DOI：

  10.1021/np800088a

文献信息

• Natural Products Chemistry and Taxonomy of the Marine Cyanobacterium <i>Blennothrix cantharidosmum</i>
  作者：Benjamin R. Clark、Niclas Engene、Margaret E. Teasdale、David C. Rowley、Teatulohi Matainaho、Frederick A. Valeriote、William H. Gerwick

  DOI：10.1021/np800088a

  日期：2008.9.1

  A Papua New Guinea field collection of the marine cyanobacterium Blennothrix cantharidosmum was investigated for its cytotoxic constituents. Bioassay-guided isolation defined the cytotoxic components as the known compounds lyngbyastatins 1 and 3. However, six new acyl proline derivatives, tumonoic acids D-I, plus the known tumonoic acid A were also isolated. Their planar structures were defined from NMR and MS data, while their stereostructures followed from a series of chiral chromatographies, degradation sequences, and synthetic approaches. The new compounds were tested in all array of assays, but showed only modest antimalarial and inhibition of quorum sensing activities. Nevertheless, these are the first natural products to be reported from this genus. and this inspired a detailed morphologic and 16S rDNA-based phylogenetic analysis of the producing organism.