2-(naphthalen-2-yl)acetyl-D-Phe-D-PheTyr(phosphate) | 959465-07-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(naphthalen-2-yl)acetyl-D-Phe-D-PheTyr(phosphate)
• 英文别名: (2S)-2-[[(2R)-2-[[(2R)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-3-(4-phosphonooxyphenyl)propanoic acid
• CAS: 959465-07-7
• 化学式: C₃₉H₃₈N₃O₉P
• 分子量: 723.719
• InChiKey: XHYHCCUSRPNVAU-VATRIRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  191
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-yl)acetyl-D-Phe-D-PheTyr(phosphate) 在 alkaline phosphatase 作用下， 以 phosphate buffer 为溶剂， 生成 (2S)-3-(4-hydroxyphenyl)-2-[[(2R)-2-[[(2R)-2-[(2-naphthalen-2-ylacetyl)amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]propanoic acid
  参考文献：
  名称：

  Using Congo red to report intracellular hydrogelation resulted from self-assembly of small molecules

  摘要：

  这篇通讯报道了利用刚果红染色自组装小分子纳米纤维来检测细胞内超分子水凝胶，为探索细胞内的分子自组装提供了一种便捷的方法。

  DOI：

  10.1039/b712971h
• 作为产物：
  描述：

  2-(naphthalen-2-y)acetyl-D-Phe-D-Phe 、 L-磷酸酪氨酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 碳酸氢钠 作用下， 以 氯仿 、 水 、 丙酮 为溶剂， 反应 3.0h， 以53.8%的产率得到2-(naphthalen-2-yl)acetyl-D-Phe-D-PheTyr(phosphate)
  参考文献：
  名称：

  Using Congo red to report intracellular hydrogelation resulted from self-assembly of small molecules

  摘要：

  这篇通讯报道了利用刚果红染色自组装小分子纳米纤维来检测细胞内超分子水凝胶，为探索细胞内的分子自组装提供了一种便捷的方法。

  DOI：

  10.1039/b712971h

文献信息

• Using Congo red to report intracellular hydrogelation resulted from self-assembly of small molecules
  作者：Gaolin Liang、Keming Xu、Lihua Li、Ling Wang、Yi Kuang、Zhimou Yang、Bing Xu

  DOI：10.1039/b712971h

  日期：——

  This communication reports the use of Congo red to stain the nanofibers of self-assembled small molecules for assaying intracellular supramolecular hydrogels, which provides a convenient method to explore molecular self-assembly inside cells.

  这篇通讯报道了利用刚果红染色自组装小分子纳米纤维来检测细胞内超分子水凝胶，为探索细胞内的分子自组装提供了一种便捷的方法。
• <scp>d</scp>-Amino Acids Modulate the Cellular Response of Enzymatic-Instructed Supramolecular Nanofibers of Small Peptides
  作者：Junfeng Shi、Xuewen Du、Dan Yuan、Jie Zhou、Ning Zhou、Yibing Huang、Bing Xu

  DOI：10.1021/bm5010355

  日期：2014.10.13

  Peptides made of d-amino acids, as the enantiomer of corresponding l-peptides, are able to resist proteolysis. It is, however, unclear or much less explored whether or how d-amino acids affect the cellular response of supramolecular nanofibers formed by enzyme-triggered self-assembly of d-peptides. In this work, we choose a cell compatible molecule, Nap-l-Phe-l-Phe-l-pTyr (LLL-1P), and systematically replace the l-amino acids in this tripeptidic precursor or its hydrogelator by the corresponding d-amino acid(s). The replacement of even one d-amino acid in this tripeptidic precursor increases its proteolytic resistance. The results of static light scattering and TEM images show the formation of nanostructures upon the addition of alkaline phosphatase, even at concentrations below the minimum gelation concentration (mgc). All these isomers are able to form ordered nanostructures and exhibit different morphologies. According to the cell viability assay on these stereochemical isomers, cells exhibit drastically different responses to the enantiomeric precursors, but almost same responses to the enantiomeric hydrogelators. Furthermore, the different cellular responses of LLL-1P and DDD-1P largely originate from the ecto-phosphatases catalyzed self-assembly of DDD-1 on the surface of cells. Therefore, this report not only illustrates a new way for tailoring the properties of supramolecular assemblies, but also provides new insights to answering the fundamental question of how mammalian cells respond to enzymatic formation of nanoscale supramolecular assemblies (e.g., nanofibers) of d-peptides.