6,7-dichloro-L-tryptophan | 1073731-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,7-dichloro-L-tryptophan
• 英文别名: 6,7-diCl-L-Trp；(2S)-2-azaniumyl-3-(6,7-dichloro-1H-indol-3-yl)propanoate
• CAS: 1073731-43-7
• 化学式: C₁₁H₁₀Cl₂N₂O₂
• 分子量: 273.119
• InChiKey: FWPPTMJFWIEUPY-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-acetyl-6,7-dichloro-DL-tryptophan 在 草酰氯 、 amano-L-acylase 作用下， 以 水 为溶剂， 生成 6,7-dichloro-L-tryptophan
  参考文献：
  名称：

  Tandem Action of the O₂- and FADH₂-Dependent Halogenases KtzQ and KtzR Produce 6,7-Dichlorotryptophan for Kutzneride Assembly

  摘要：

  Kutznerides are actinomycete-derived antifungal nonribosomal hexadepsipeptides which are assembled from five unsual nonproteinogenic amino acids and one hydroxy acid. Conserved in all structurally characterized kutznerides is a dichlorinated tricyclic hexahydropyrroloindole postulated to be derived from 6,7-dichlorotryptophan. In this Communication, we identify KtzQ and KtzR as tandem acting FADH(2)-dependent halogenases that work sequentially on free L-tryptophan to generate 6,7-dichloro-L-tryptophan. Kinetic characterization of these two enzymes has shown that KtzQ (along with the flavin reductase KtzS) acts first to chlorinate at the 7-position of L-tryptophan. KtZR, with a similar to 120 fold preference for 7-chloro-L-tryptophan over L-tryptophan, then installs the second chlorine at the 6-position of 7-chloro-L-tryptophan to generate 6,7-dichloro-L-tryptophan. These findings provide further insights into the enzymatic logic of carbon-chloride bond formation during the biosynthesis of halogenated secondary metabolites.

  DOI：

  10.1021/ja806467a