[3-2H]-(3R)-3-hydroxyglutaric acid monopropyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: [3-2H]-(3R)-3-hydroxyglutaric acid monopropyl ester
• 化学式: C₈H₁₄O₅
• 分子量: 191.188
• InChiKey: RKTGILKIKVINAC-DUVJLBCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,3-丙酮二羧酸 在 镍 盐酸 、 三乙胺 、 氘 作用下， 以 丙醇 、 phosphate buffer 为溶剂， 反应 62.0h， 生成 [3-2H]-(3R)-3-hydroxyglutaric acid monopropyl ester
  参考文献：
  名称：

  Biosynthetic Precursors of the Lipase Inhibitor Lipstatin

  摘要：

  Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy. [3,10,11,12-H-2]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-H-2(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [C-13-formyl,N-15]-N-formylleucine (10) was diverted to lipstatin under loss of the C-13-labeled formyl residue.

  DOI：

  10.1021/jo016285v

文献信息

• Biosynthetic Precursors of the Lipase Inhibitor Lipstatin
  作者：Christoph A. Schuhr、Wolfgang Eisenreich、Markus Goese、Peter Stohler、Wolfgang Weber、Ernst Kupfer、Adelbert Bacher

  DOI：10.1021/jo016285v

  日期：2002.4.1

  Three putative intermediates in the biosynthesis of the lipase inhibitor lipstatin were synthesized in stable isotope-labeled form and were added to fermentation cultures of Streptomyces toxytricini. Biosynthetic lipstatin was isolated and analyzed by NMR spectroscopy. [3,10,11,12-H-2]-(3S,5Z,8Z)-3-hydroxytetradeca-5,8-dienoic acid (9) was shown to serve as a direct biosynthetic precursor of lipstatin. [7,8-H-2(2)]Hexylmalonate (11) was also incorporated into lipstatin, albeit at a relatively low rate. The leucine moiety of [C-13-formyl,N-15]-N-formylleucine (10) was diverted to lipstatin under loss of the C-13-labeled formyl residue.