γ-(6-chlorohexyl)-L-glutamic acid N-carboxyanhydride | 1380074-47-4

• 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: γ-(6-chlorohexyl)-L-glutamic acid N-carboxyanhydride
• 英文别名: 6-chlorohexyl 3-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]propanoate
• CAS: 1380074-47-4
• 化学式: C₁₂H₁₈ClNO₅
• 分子量: 291.732
• InChiKey: RUWMSFIJFANDHA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  光气 、 γ-(6-chlorohexyl)-L-glutamate 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以83%的产率得到γ-(6-chlorohexyl)-L-glutamic acid N-carboxyanhydride
  参考文献：
  名称：

  [EN] ANTIMICROBIAL ALPHA-HELICAL CATIONIC POLYPEPTIDES
  [FR] POLYPEPTIDES CATIONIQUES ALPHA-HÉLICOÏDAUX ANTIMICROBIENS

  摘要：

  该发明提供了具有高径向亲疏水性的抗菌多肽（AMPs）。与典型的具有表面亲疏水性的AMPs或具有随机分布带电和疏水基团的仿生抗菌聚合物不同，这些新的AMPs是具有径向亲疏水结构的同源多肽。它们采用稳定的α-螺旋构象，具有疏水螺旋核心和带电外壳，由具有末端带电基团的柔性疏水侧链形成。径向亲疏水多肽相对于传统AMPs具有多个优势，包括对蛋白酶的稳定性和设计的简单性。它们还表现出对革兰氏阴性和革兰氏阳性细菌的高抗菌活性和低溶血活性。因此，这些AMPs为治疗耐药细菌感染提供了一个通用平台。

  公开号：

  WO2016210442A1

文献信息

• Helical poly(arginine) mimics with superior cell-penetrating and molecular transporting properties
  作者：Haoyu Tang、Lichen Yin、Kyung Hoon Kim、Jianjun Cheng

  DOI：10.1039/c3sc51328a

  日期：——

  Poly(arginine) mimics bearing long hydrophobic side chains adopt a stable helical conformation and exhibit helix-related cell-penetrating properties. Elongating the polypeptide backbone length and increasing side chain hydrophobicity further increase the helicities of poly(arginine) mimics. These helical poly(arginine) mimics show superior cell membrane permeability up to two orders of magnitude higher than that of HIV-TAT peptide and excellent DNA and siRNA delivery efficiencies in various mammalian cells.

  带有长疏水侧链的聚（精氨酸）模拟物采用稳定的螺旋构象并表现出与螺旋相关的细胞穿透特性。延长多肽主链长度和增加侧链疏水性进一步增加聚（精氨酸）模拟物的螺旋度。这些螺旋聚（精氨酸）模拟物表现出优异的细胞膜渗透性，比 HIV-TAT 肽高出两个数量级，并且在各种哺乳动物细胞中具有出色的 DNA 和 siRNA 递送效率。
• Antimicrobial alpha-helical cationic polypeptides
  申请人：The Board of Trustees of the University of Illinois

  公开号：US11124605B2

  公开（公告）日：2021-09-21

  The invention provides antimicrobial polypeptides (AMPs) with high radial amphiphilicity. Unlike typical AMPs characterized by facial amphiphilicity or biomimetic antimicrobial polymers with randomly distributed charged and hydrophobic groups, these new AMPs are homo-polypeptides with radially amphiphilic structure. They adopt a stable α-helical conformation with a hydrophobic helical core and a charged exterior shell, formed by flexible hydrophobic side chains with terminal charge group. The radially amphiphilic polypeptides offer several advantages over conventional AMPs with regard to stability against protease and simplicity of design. They also exhibit high antibacterial activity against both Gram-negative and Gram-positive bacteria and low hemolytic activity. The AMPs thus provide a general platform for treating drug-resistant bacterial infections.

  本发明提供了具有高径向两亲性的抗菌多肽（AMPs）。与典型的表面两亲性抗菌多肽或具有随机分布的带电和疏水基团的仿生物抗菌聚合物不同，这些新型抗菌多肽是具有径向两亲性结构的同源多肽。它们采用稳定的 α 螺旋构象，具有疏水螺旋核心和带电外壳，外壳由带末端电荷基团的柔性疏水侧链形成。与传统的蛋白胨相比，径向两亲多肽在抗蛋白酶稳定性和设计简便性方面具有多项优势。它们对革兰氏阴性菌和革兰氏阳性菌都具有很高的抗菌活性，而且溶血活性较低。因此，AMP 为治疗耐药性细菌感染提供了一个通用平台。
• Polypeptides with Quaternary Phosphonium Side Chains: Synthesis, Characterization, and Cell-Penetrating Properties
  作者：Ziyuan Song、Nan Zheng、Xiaochu Ba、Lichen Yin、Rujing Zhang、Liang Ma、Jianjun Cheng

  DOI：10.1021/bm5001026

  日期：2014.4.14

  Polypeptides bearing quaternary phosphonium side chains were synthesized via controlled ring-opening polymerization of chlorine-functionalized amino acid N-carboxyanhydride monomers followed by one-step nucleophilic substitution reaction with triethylphosphine. The conformation of the resulting polypeptides can be controlled by modulating the side-chain length and alpha-carbon stereochemistry. The phosphonium-based poly(L-glutamate) derivatives with 11 sigma-bond backbone-to-charge distance adopt stable alpha-helical conformation against pH and ionic strength changes. These helical, quaternary phosphonium-bearing polypeptides exhibit higher cell-penetrating capability than their racemic and random-coiled analogues. They enter cells mainly via an energy-independent, nonendocytic cell membrane transduction mechanism and exhibit low cytotoxicity, substantiating their potential use as a safe and effective cell-penetrating agent.
• ANTIMICROBIAL ALPHA-HELICAL CATIONIC POLYPEPTIDES
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20180179336A1

  公开（公告）日：2018-06-28

  The invention provides antimicrobial polypeptides (AMPs) with high radial amphiphilicity. Unlike typical AMPs characterized by facial amphiphilicity or biomimetic antimicrobial polymers with randomly distributed charged and hydrophobic groups, these new AMPs are homo-polypeptides with radially amphiphilic structure. They adopt a stable α-helical conformation with a hydrophobic helical core and a charged exterior shell, formed by flexible hydrophobic side chains with terminal charge group. The radially amphiphilic polypeptides offer several advantages over conventional AMPs with regard to stability against protease and simplicity of design. They also exhibit high antibacterial activity against both Gram-negative and Gram-positive bacteria and low hemolytic activity. The AMPs thus provide a general platform for treating drug-resistant bacterial infections.