deamino-Abu(N3)-Gly-Val-Gly-Val-OMe | 1427273-29-7

• 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: deamino-Abu(N3)-Gly-Val-Gly-Val-OMe
• 英文别名: methyl (2S)-2-[[2-[[(2S)-2-[[2-(4-azidobutanoylamino)acetyl]amino]-3-methylbutanoyl]amino]acetyl]amino]-3-methylbutanoate
• CAS: 1427273-29-7
• 化学式: C₁₉H₃₃N₇O₆
• 分子量: 455.514
• InChiKey: SHZSKUHTETTXIY-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  deamino-Abu(N3)-Gly-Val-Gly-Val-OMe 、 7-(propynyloxy)-2H-chromen-2-one 在 copper(II) sulfate 、 维生素 C 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-3-methyl-2-[[2-[[(2S)-3-methyl-2-[[2-[4-[4-[(2-oxochromen-7-yl)oxymethyl]triazol-1-yl]butanoylamino]acetyl]amino]butanoyl]amino]acetyl]amino]butanoate
  参考文献：
  名称：

  Tetrapeptide–coumarin conjugate 3D networks based on hydrogen-bonded charge transfer complexes: gel formation and dye release

  摘要：

  寡肽衍生物是生物基功能材料的重要合成子。在本文中，合成了 Gly-(L-Val)-Gly-(L-Val)·香豆素 (GVGV·Cou) 缀合物，它在乙醇中形成 3D 网络。通过紫外-可见光谱、傅里叶变换红外光谱、X射线衍射(XRD)、SEM和TEM对凝胶纳米结构进行了表征。这表明香豆素部分之间电荷转移（CT）复合物的形成是凝胶形成的主要驱动力。探索了凝胶封装和释放染料的能力。刚果红 (CR) 和亚甲蓝 (MB) 都可以被捕获在 CT 凝胶基质中并随着时间的推移而释放。本凝胶可用作客体封装和释放的功能性软材料。

  DOI：

  10.1039/c5sm00995b
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 deamino-Abu(N3)-Gly-Val-Gly-Val-OMe
  参考文献：
  名称：

  A clickable, highly soluble oligopeptide that easily forms organogels

  摘要：

  An artificial peptide, N-3-GVGV-OMe (G, glycine; V, valine), which mimics the repeating GAGA (A, alanine) sequence in Bombix Mori silk, was synthesised via solution-phase synthesis. Compared with N-3-GAGA-OMe sequence, N-3-GVGV-OMe showed high solubility in common organic solvents (such as CHCl3, THF and CH2Cl2), and easily formed organogels simply by adding poor solvents (such as toluene or ether) to the peptide solution at room temperature. The hierarchical nanostructure of N-3-GVGV-OMe organogel was dependent on the nature of the poor solvents, although in all cases, -sheets were formed exclusively. Gels formed in ether showed higher level hierarchical assembly, as evidenced by AFM and CD studies. Solution-state FT-IR analysis showed that the pre-organisation of the peptides in solution was not significant, and well-defined antiparallel -sheets were formed after the addition of the poor solvent. The high solubility and strong tendency for self-assembly of N-3-GVGV-OMe, together with its terminal azide group, might facilitate the modification of functional organic molecules even macromolecules for better nanostructure control.

  DOI：

  10.1080/10610278.2013.766735

文献信息

• Polythiophene with oligopeptide side chain: preparation and nano-structure
  作者：Xiao Wang、Ruiying Gong、Yubao Song、Ming Li、Youbing Mu、Zongxia Guo、Xiaobo Wan、Wei Jiang

  DOI：10.1080/10610278.2013.809086

  日期：2013.12.1

  This manuscript describes the first example of nanorods formation of an oligopeptide-modified polythiophene (PTh). The oligopeptide-modified monomer was carefully engineered in such a way to keep both high solubility and the ability for self-assembly. A terthiophene with a clickable side chain on the middle thiophene ring and two octyl side chains on the terminal thiophene rings was synthesised to guarantee the solubility; a tetrapeptide (N-3-GVGV-OMe) was chosen to provide self-assembly capability. The monomer obtained by click chemistry showed both high solubility and the ability to form organogels. The monomer was easily polymerised either in solution state or in organogel state to give the corresponding PTh with oligopeptide side chain. The size of the nanorods could be controlled by adjusting the reaction conditions. The formation of the nano-structure was attributed to the H-bonding between oligopeptide side chain and its interaction with Fe (II) ion.
• A clickable, highly soluble oligopeptide that easily forms organogels
  作者：Ruiying Gong、Yubao Song、Zongxia Guo、Ming Li、Yi Jiang、Xiaobo Wan

  DOI：10.1080/10610278.2013.766735

  日期：2013.5.1

  An artificial peptide, N-3-GVGV-OMe (G, glycine; V, valine), which mimics the repeating GAGA (A, alanine) sequence in Bombix Mori silk, was synthesised via solution-phase synthesis. Compared with N-3-GAGA-OMe sequence, N-3-GVGV-OMe showed high solubility in common organic solvents (such as CHCl3, THF and CH2Cl2), and easily formed organogels simply by adding poor solvents (such as toluene or ether) to the peptide solution at room temperature. The hierarchical nanostructure of N-3-GVGV-OMe organogel was dependent on the nature of the poor solvents, although in all cases, -sheets were formed exclusively. Gels formed in ether showed higher level hierarchical assembly, as evidenced by AFM and CD studies. Solution-state FT-IR analysis showed that the pre-organisation of the peptides in solution was not significant, and well-defined antiparallel -sheets were formed after the addition of the poor solvent. The high solubility and strong tendency for self-assembly of N-3-GVGV-OMe, together with its terminal azide group, might facilitate the modification of functional organic molecules even macromolecules for better nanostructure control.
• Tetrapeptide–coumarin conjugate 3D networks based on hydrogen-bonded charge transfer complexes: gel formation and dye release
  作者：Zongxia Guo、Ruiying Gong、Yi Jiang、Xiaobo Wan

  DOI：10.1039/c5sm00995b

  日期：——

  Oligopeptide-based derivatives are important synthons for bio-based functional materials. In this article, a Gly-(L-Val)-Gly-(L-Val)–coumarin (GVGV–Cou) conjugate was synthesized, which forms 3D networks in ethanol. The gel nanostructures were characterized by UV-vis spectroscopy, FT-IR spectroscopy, X-ray diffraction (XRD), SEM and TEM. It is suggested that the formation of charge transfer (CT) complexes between the coumarin moieties is the main driving force for the gel formation. The capability of the gel to encapsulate and release dyes was explored. Both Congo Red (CR) and Methylene Blue (MB) can be trapped in the CT gel matrix and released over time. The present gel might be used as a functional soft material for guest encapsulation and release.

  寡肽衍生物是生物基功能材料的重要合成子。在本文中，合成了 Gly-(L-Val)-Gly-(L-Val)·香豆素 (GVGV·Cou) 缀合物，它在乙醇中形成 3D 网络。通过紫外-可见光谱、傅里叶变换红外光谱、X射线衍射(XRD)、SEM和TEM对凝胶纳米结构进行了表征。这表明香豆素部分之间电荷转移（CT）复合物的形成是凝胶形成的主要驱动力。探索了凝胶封装和释放染料的能力。刚果红 (CR) 和亚甲蓝 (MB) 都可以被捕获在 CT 凝胶基质中并随着时间的推移而释放。本凝胶可用作客体封装和释放的功能性软材料。