18₂DGA-GGG-OCH2Ph | 407629-40-7

• 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: 18₂DGA-GGG-OCH2Ph
• 英文别名: (C18H37)2NCOCH2OCH2CO-Gly-Gly-Gly-OCH2Ph；benzyl 2-[[2-[[2-[[2-[2-(dioctadecylamino)-2-oxoethoxy]acetyl]amino]acetyl]amino]acetyl]amino]acetate
• CAS: 407629-40-7
• 化学式: C₅₃H₉₄N₄O₇
• 分子量: 899.352
• InChiKey: AZAPLSIESNHZQU-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42 °C(Solv: methanol (67-56-1))
• 沸点：
  960.9±65.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  16.7
• 重原子数：
  64
• 可旋转键数：
  47
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  18₂DGA-GGG-OCH2Ph 在 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、413.7 kPa 条件下， 反应 54.5h， 生成 18₂[DGA]-GGGPGGG-OH
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR SYNTHETIC AMPHIPHILE-INDUCED CHANGES IN PLANT ROOT MORPHOLOGY
  [FR] COMPOSITIONS ET PROCÉDÉS POUR MODIFICATIONS DE MORPHOLOGIE DE RACINES DE PLANTE INDUITES PAR AMPHIPHILE SYNTHÉTIQUE

  摘要：

  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。

  公开号：

  WO2016022991A1
• 作为产物：
  描述：

  双十八烷基胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 18₂DGA-GGG-OCH2Ph
  参考文献：
  名称：

  Replacing proline at the apex of heptapeptide-based chloride ion transporters alters their properties and their ionophoretic efficacy

  摘要：

  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。

  DOI：

  10.1039/b206570n

文献信息

• Fluorescent, Synthetic Amphiphilic Heptapeptide Anion Transporters: Evidence for Self‐Assembly and Membrane Localization in Liposomes
  作者：Lei You、George W. Gokel

  DOI：10.1002/chem.200800147

  日期：2008.6.27

  Synthetic anion transporters (SATs) of the general type (n-C18H37)2N-COCH2OCH2CO-(Gly)3-Pro-(Gly)3-O-n-C7H15, 1, are amphiphilic peptides that form anion-conducting pores in bilayer membranes. To better understand membrane insertion, assembly and aggregation dynamics, and membrane penetration, four novel fluorescent structures were prepared for use in both aqueous buffer and phospholipid bilayers.

  一般类型 (n-C18H37)2N-COCH2OCH2CO-(Gly)3-Pro-(Gly)3-On-C7H15, 1 的合成阴离子转运蛋白 (SAT) 是两亲性肽，在双层膜中形成阴离子传导孔。为了更好地了解膜插入、组装和聚集动力学以及膜渗透，制备了四种新型荧光结构，用于水性缓冲液和磷脂双层。将荧光残基芘、吲哚、丹酰基和NBD掺入1中，分别得到2、3、4和5。通过监测 2 观察到的芘单体/准分子峰的变化，证实了缓冲液中肽两亲物的组装。双层中吲哚 (3) 和丹磺酰 (4) 侧链 SAT 观察到的溶剂依赖性荧光变化表明，这些残基经历了极性介于 epsilon=9 (CH2Cl2) 和 epsilon=24 (EtOH) 之间的环境。 2 和 3 之间的荧光共振能量转移 (FRET) 表明 SAT 单体在双层内聚集。这种自组装导致孔的形成，这被检测为 Cl(-) 从脂质体中释放。荧光 SAT 的丙烯酰胺猝灭结果支持膜插入。
• The C-and N-terminal residues of synthetic heptapeptide ion channels influence transport efficacy through phospholipid bilayers
  作者：Natasha Djedovi?、Riccardo Ferdani、Egan Harder、Jolanta Pajewska、Robert Pajewski、Michelle E. Weber、Paul H. Schlesinger、George W. Gokel

  DOI：10.1039/b417091c

  日期：——

  The synthetic peptide, R2N-COCH2OCH2CO-Gly-Gly-Gly-Pro-Gly-Gly-Gly-OR′, was shown to be selective for Cl− over K+ when R is n-octadecyl and R′ is benzyl. Nineteen heptapeptides have now been prepared in which the N-terminal and C-terminal residues have been varied. All of the N-terminal residues are dialkyl but the C-terminal chains are esters, 2° amides, or 3° amides. The compounds having varied N-terminal anchors and C-terminal benzyl groups are as follows: 1, R = n-propyl; 2, R = n-hexyl; 3, R = n-octyl; 4, R = n-decyl; 5, R = n-dodecyl; 6, R = n-tetradecyl; 7, R = n-hexadecyl; 8, R = n-octadecyl. Compounds 9–19 have R = n-octadecyl and C-terminal residues as follows: 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. The highest anion transport activities were observed as follows. For the benzyl esters whose N-terminal residues were varied, i.e.1–8, compound 3 was most active. For the C18 anchored esters 10–14, n-heptyl ester 11 was most active. For the C18 anchored, C-terminal amides 15–19, di-n-decylamide 17 was most active. It was concluded that both the C-and N-terminal anchors were important for channel function in the bilayer but that activity was lost unless only one of the two anchoring groups was dominant.

  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。
• 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/
  作者：Paul H. Schlesinger、Riccardo Ferdani、Robert Pajewski、Jolanta Pajewska、George W. Gokel

  DOI：10.1039/b200126h

  日期：2002.4.11

  The heptapeptide sequence Gly-Gly-Gly-Pro-Gly-Gly-Gly, when anchored to diglycolic acid derived (C18H37)2NCOCH2OCH2COOH, forms chloride-selective ion channels in phospholipid liposomes but the related heptapeptide Gly-Gly-Gly-Leu-Gly-Gly-Gly, and tripeptide Gly-Gly-Gly do not.

  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。
• 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。
• Synthetic ion channels
  申请人：Washington University

  公开号：US20030176641A1

  公开（公告）日：2003-09-18

  The design, synthesis, and characterization of synthetic anion membrane transporters are presented. These novel compounds impart ion permeability to phospholipid bilayers and also modulate cellular volume in mammalian cells in vitro. The compounds insert rapidly into liposomes and planar lipid bilayers.

  介绍了合成阴离子膜转运体的设计、合成和表征。这些新型化合物赋予磷脂双层离子渗透性，并在体外哺乳动物细胞中调节细胞体积。这些化合物能够快速插入到脂质体和平面脂质双层中。