L-tryptophanoyl-CoA | 1282523-20-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: L-tryptophanoyl-CoA
• CAS: 1282523-20-9
• 化学式: C₃₂H₄₆N₉O₁₇P₃S
• 分子量: 953.755
• InChiKey: UFMRCTGEYQRSER-PTDZNDCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.28
• 重原子数：
  62.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  405.44
• 氢给体数：
  11.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  L-tryptophanoyl-CoA 、 丙二酰辅酶A-钠盐 在 乙二胺四乙酸 、 benzalacetone synthase 、 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 以6.7%的产率得到(2'S,5S)-2',5-bis((1H-indol-3-yl)methyl)-4-hydroxy-1H,1'H-[3,3'-bipyrrole]-2,5'(2'H,5H)-dione
  参考文献：
  名称：

  Cytotoxic Tetramic Acid Derivative Produced by a Plant Type-III Polyketide Synthase

  摘要：

  The tetramic acid (2,4-pyrrolidinedione) scaffold has been recognized as an important structural feature because of its mycotoxic, antibacterial, antiviral, and antioxidant activities. This important class of natural products is reportedly produced by the type-I polyketide synthase/nonribosomal peptide synthetase (PKS/NRPS) hybrid megaenzyme systems. In contrast, the benzalacetone synthase (BAS) from Rheum palmatum is a structurally simple, plant-specific type-III PKS that catalyzes the one-step decarboxylative condensation of malonyl-CoA with 4-coumaroyl-CoA. The type-III PKS exhibits unusually broad substrate specificity and notable catalytic versatility. Here we report that R. palmatum BAS efficiently produces a series of unnatural, novel tetramic acid derivatives by the condensation of malonyl-CoA with aminoacyl-CoA thioesters chemically synthesized from L- and D-amino acids. Remarkably, the novel tetramic acid dimer ID-S formed from D-phenylalanoyl-CoA showed moderate antiproliferative activity against murine leukemia P388 cells.

  DOI：

  10.1021/ja2006737