[2-(2-{[1-(2-{2-[2-(2-dioctadecylcarbamoylmethoxyacetylamino)acetylamino]acetylamino}acetyl)pyrrolidine-2-carbonyl]amino}acetylamino)acetylamino]acetic acid benzyl ester | 407629-44-1

• 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-(2-{[1-(2-{2-[2-(2-dioctadecylcarbamoylmethoxyacetylamino)acetylamino]acetylamino}acetyl)pyrrolidine-2-carbonyl]amino}acetylamino)acetylamino]acetic acid benzyl ester
• 英文别名: 18₂[DGA]-GGGPGGG-OCH2Ph；18₂-[DGA]-GGGPGGG-OCH2Ph；benzyl 2-[[2-[[2-[[(2S)-1-[2-[[2-[[2-[[2-[2-(dioctadecylamino)-2-oxoethoxy]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]acetyl]amino]acetyl]amino]acetate
• CAS: 407629-44-1
• 化学式: C₆₄H₁₁₀N₈O₁₁
• 分子量: 1167.62
• InChiKey: DCAXVZHQIVTJSS-GNFJTHHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.8
• 重原子数：
  83
• 可旋转键数：
  54
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  251
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [2-(2-{[1-(2-{2-[2-(2-dioctadecylcarbamoylmethoxyacetylamino)acetylamino]acetylamino}acetyl)pyrrolidine-2-carbonyl]amino}acetylamino)acetylamino]acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以94%的产率得到18₂[DGA]-GGGPGGG-OH
  参考文献：
  名称：

  The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers

  摘要：

  合成肽R2N-COCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR′在R为n-十八烷基且R′为苄基时，对Cl−相对于K+表现出选择性。目前已制备出十九种七肽，其中N端和C端残基有所不同。所有N端残基均为二烷基，而C端链为酯、二级酰胺或三级酰胺。N端锚和C端苄基不同的化合物如下：1，R = n-丙基；2，R = n-己基；3，R = n-戊基；4，R = n-癸基；5，R = n-十二烷基；6，R = n-十四烷基；7，R = n-十六烷基；8，R = n-十八烷基。化合物9–19中R = n-十八烷基，C端残基如下：9，OR′ = OCH2CH3；10，OR′ = OCH(CH3)2；11，OR′ = O(CH2)6CH3；12，OR′ = OCH2–c-C6H11；13，OR′ = O(CH2)9CH3；14，OR′ = O(CH2)17CH3；15，NR′2 = N[(CH2)6CH3]2；16，NHR′ = NH(CH2)9CH3；17，NR′2 = N[(CH2)9CH3]2；18，NHR′ = NH(CH2)17CH3；19，NR′2 = N[(CH2)17CH3]2。观察到的最高阴离子转运活性如下：对于N端残基变量的苄基酯，i.e.1–8，化合物3活性最强。对于C18锚定的酯10–14，n-庚基酯11活性最强。对于C18锚定的C端酰胺15–19，二-n-癸酰胺17活性最强。结论是C端和N端锚对双层膜中的通道功能十分重要，但只有其中一个锚定基团占主导时活性才存在。

  DOI：

  10.1039/b417091c
• 作为产物：
  描述：

  dioctadecylcarbamoylmethoxyacetic acid 在 palladium on activated charcoal 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 60.0h， 生成 [2-(2-{[1-(2-{2-[2-(2-dioctadecylcarbamoylmethoxyacetylamino)acetylamino]acetylamino}acetyl)pyrrolidine-2-carbonyl]amino}acetylamino)acetylamino]acetic acid benzyl ester
  参考文献：
  名称：

  A hydrocarbon anchored peptide that forms a chloride-selective channel in liposomesElectronic supplementary information (ESI) available: analytical data for 1, 2 and 3. See http://www.rsc.org/suppdata/cc/b2/b200126h/

  摘要：

  七肽序列Gly-Gly-Gly-Pro-Gly-Gly-Gly，当锚定于由二甘醇酸衍生的（C18H37）2NCOCH2OCH2COOH上时，能在磷脂脂质体中形成氯离子选择性离子通道，但相关的七肽Gly-Gly-Gly-Leu-Gly-Gly-Gly和三肽Gly-Gly-Gly则不能。

  DOI：

  10.1039/b200126h

文献信息

• [EN] COMPOSITIONS AND METHODS FOR SYNTHETIC AMPHIPHILE-INDUCED CHANGES IN PLANT ROOT MORPHOLOGY<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR MODIFICATIONS DE MORPHOLOGIE DE RACINES DE PLANTE INDUITES PAR AMPHIPHILE SYNTHÉTIQUE
  申请人：UNIV MISSOURI

  公开号：WO2016022991A1

  公开（公告）日：2016-02-11

  The disclosure provides a method for increasing the lateral root development of a plant by exposing said plant to a composition containing a synthetic amphiphile. By increasing the number of lateral roots, the surface area of the root structure is increased, making the plants better able to survive such stresses as drought or low nutrients

  该公开提供了一种通过将植物暴露在含有合成两性分子的组合物中来增加植物侧根发育的方法。通过增加侧根的数量，根结构的表面积增加，使植物更能够抵抗干旱或低营养等压力。
• Replacing proline at the apex of heptapeptide-based chloride ion transporters alters their properties and their ionophoretic efficacy
  作者：Paul H. Schlesinger、Riccardo Ferdani、Jolanta Pajewska、Robert Pajewski、George W. Gokel

  DOI：10.1039/b206570n

  日期：2003.1.8

  A membrane anchored heptapeptide, (C18H37)2NHCOCH2OCH2CO–NH–Gly–Gly–Gly–Pro–Gly–Gly–Gly–OCH2Ph, has proved to be a selective chloride anion transporter that functions in phospholipid bilayer membranes. When Pro was replaced by the natural amino acid Leu, the activity decreased dramatically. In the present study, Pro is replaced by pipecolic acid (homoproline, Pip); the resulting anchored heptapeptide is a membrane active, chloride selective transporter.

  一种锚定在膜上的七肽(C18H37)2NHCOCH2OCH2CO–NH–Gly–Gly–Gly–Pro–Gly–Gly–Gly–OCH2Ph已被证明是一种选择性氯阴离子转运体，能够在磷脂双层膜中发挥作用。当Pro被天然氨基酸Leu替换时，活性显著降低。在本研究中，Pro被哌嗪酸（同脯氨酸，Pip）替换，所得到的锚定七肽是一种膜活性的氯选择性转运体。
• The C-terminal ester of membrane anchored peptide ion channels affects anion transport
  作者：Natasha Djedovic、Riccardo Ferdani、Egan Harder、Jolanta Pajewska、Robert Pajewski、Paul H. Schlesinger、George W. Gokel

  DOI：10.1039/b312209n

  日期：——

  Five heptapeptide derivatives, [CH3(CH2)17]2NCOCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR, in which R = ethyl, 2-propyl, heptyl, benzyl, and cyclohexylmethyl, were found to transport chloride anion through a phospholipid bilayer to varying extents dependent on the identity of R. It was concluded that the R group is a membrane anchor for the synthetic chloride channels.

  研究发现，[CH3(CH2)17]2NCO O CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR（其中 R =乙基、2-丙基、庚基、苄基和环己基甲基）等五种七肽衍生物可通过磷脂双分子层转运氯离子，转运程度因 R 的特性而异。
• Evidence for dimer formation by an amphiphilic heptapeptide that mediates chloride and carboxyfluorescein release from liposomes
  作者：Robert Pajewski、Riccardo Ferdani、Jolanta Pajewska、Natasha Djedovi?、Paul H. Schlesinger、George W. Gokel

  DOI：10.1039/b417009a

  日期：——

  Heptapeptides having dioctadecyl, N-terminal hydrocarbon chains insert in phospholipid bilayer membranes and form pores through which at least chloride ions pass. Although amphiphilic, these compounds do not typically form vesicles themselves. They insert in the bilayers of phospholipid vesicles and mediate the release of carboxyfluorescein. Hill analysis indicates that at least two molecules of the amphiphile are involved in pore formation. In CD2Cl2, dimer formation is detected by NMR chemical shift changes. The anion release activity of individual anion transporters is increased by linking them covalently at the C-terminus or, even more, by linking them at the N-terminus. Evidence is presented that either linked molecule releases chloride from liposomes more effectively and rapidly than the individual transporter molecule at a comparable concentration.

  具有双十八烷基 N 端碳氢链的七肽可插入磷脂双层膜并形成孔隙，至少氯离子可通过孔隙。虽然具有两亲性，但这些化合物本身通常不会形成囊泡。它们插入磷脂囊泡的双层膜，介导羧基荧光素的释放。希尔分析表明，至少有两个双亲化合物分子参与了孔的形成。在 CD2Cl2 中，二聚体的形成是通过核磁共振化学位移变化检测到的。通过在 C 端共价连接或更多地在 N 端连接，可以提高单个阴离子转运体的阴离子释放活性。有证据表明，在浓度相当的情况下，两种连接的分子从脂质体中释放氯化物的效率和速度均高于单个转运体分子。
• SCMTR:  A Chloride-Selective, Membrane-Anchored Peptide Channel that Exhibits Voltage Gating
  作者：Paul H. Schlesinger、Riccardo Ferdani、Jun Liu、Jolanta Pajewska、Robert Pajewski、Mitsuyoshi Saito、Hossein Shabany、George W. Gokel

  DOI：10.1021/ja016784d

  日期：2002.3.1

  The design, synthesis, and characterization of a synthetic chloride membrane transporter, SCMTR (synthetic chloride membrane transporter, "scimitar"), are presented. The compound [CH3(CH2)17]2NCOCH2OCH2CO-GGGPGGG-OBzl inserts rapidly into liposomes and planar lipid bilayers. SCMTR has a 1.3 +/- 0.01 nS chloride diffusion pathway (>10:1 Cl/K selectivity). Evidence was also obtained for voltage gating behavior.