1-(4-carboxybutyl)-3,3-dimethyl-2-(4-(phenylimino)but-1-en-1-yl)-3H-indol-1-ium | 1446743-44-7

• 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: 1-(4-carboxybutyl)-3,3-dimethyl-2-(4-(phenylimino)but-1-en-1-yl)-3H-indol-1-ium
• CAS: 1446743-44-7
• 化学式: C₂₅H₂₉N₂O₂
• 分子量: 389.517
• InChiKey: VZSXEAJIYFVAFF-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  52.67
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-carboxybutyl)-3,3-dimethyl-2-(4-(phenylimino)but-1-en-1-yl)-3H-indol-1-ium 在 potassium acetate 、 N,N-二异丙基乙胺 、 fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate 、 三氟乙酸 、 sodium iodide 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.33h， 生成 1-(5-(4-(6-(aminooxy)hexyl)piperazin-1-yl)-5-oxopentyl)-3,3-dimethyl-2-(5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-3H-indol-1-ium
  参考文献：
  名称：

  A General Method for Fluorescent Labeling of the N-Termini of Lanthipeptides and Its Application to Visualize their Cellular Localization

  摘要：

  Labeling of natural products with biophysical probes has greatly contributed to investigations of their modes of action and has provided tools for visualization of their targets. A general challenge is the availability of a suitable functional group for chemoselective modification. We demonstrate here that an N-terminal ketone is readily introduced into various lanthipeptides by the generation of a cryptic N-terminal dehydro amino acid by the cognate biosynthetic enzymes. Spontaneous hydrolysis of the N-terminal enamines results in alpha-ketoamides that site-specifically react with an aminooxy-derivatized alkyne or fluorophore. The methodology was successfully applied to prochlorosins 1.7 and 2.8, as well as the lantibiotics lacticin 481, haloduracin alpha, and haloduracin beta. The fluorescently modified lantibiotics were added to bacteria, and their cellular localization was visualized by confocal fluorescence microscopy. Lacticin 481 and haloduracin alpha localized predominantly at sites of new and old cell division as well as in punctate patterns along the long axis of rod-shaped bacilli, similar to the localization of lipid II. On the other hand, haloduracin beta was localized nonspecifically in the absence of haloduracin a, but formed specific patterns when coadministered with haloduracin alpha. Using two-color labeling, colocalization of both components of the two-component lantibiotic haloduracin was demonstrated. These data with living cells supports a model in which the a component recognizes lipid II and then recruits the beta-component.

  DOI：

  10.1021/ja4010706
• 作为产物：
  描述：

  5-溴戊酸 在 potassium acetate 、 乙酸酐 作用下， 反应 5.25h， 生成 1-(4-carboxybutyl)-3,3-dimethyl-2-(4-(phenylimino)but-1-en-1-yl)-3H-indol-1-ium
  参考文献：
  名称：

  A General Method for Fluorescent Labeling of the N-Termini of Lanthipeptides and Its Application to Visualize their Cellular Localization

  摘要：

  Labeling of natural products with biophysical probes has greatly contributed to investigations of their modes of action and has provided tools for visualization of their targets. A general challenge is the availability of a suitable functional group for chemoselective modification. We demonstrate here that an N-terminal ketone is readily introduced into various lanthipeptides by the generation of a cryptic N-terminal dehydro amino acid by the cognate biosynthetic enzymes. Spontaneous hydrolysis of the N-terminal enamines results in alpha-ketoamides that site-specifically react with an aminooxy-derivatized alkyne or fluorophore. The methodology was successfully applied to prochlorosins 1.7 and 2.8, as well as the lantibiotics lacticin 481, haloduracin alpha, and haloduracin beta. The fluorescently modified lantibiotics were added to bacteria, and their cellular localization was visualized by confocal fluorescence microscopy. Lacticin 481 and haloduracin alpha localized predominantly at sites of new and old cell division as well as in punctate patterns along the long axis of rod-shaped bacilli, similar to the localization of lipid II. On the other hand, haloduracin beta was localized nonspecifically in the absence of haloduracin a, but formed specific patterns when coadministered with haloduracin alpha. Using two-color labeling, colocalization of both components of the two-component lantibiotic haloduracin was demonstrated. These data with living cells supports a model in which the a component recognizes lipid II and then recruits the beta-component.

  DOI：

  10.1021/ja4010706