Boc-GGGG-OCH2Ph | 108432-90-2

• 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: Boc-GGGG-OCH2Ph
• 英文别名: Boc-Gly4-OBzl；benzyl 2,2-dimethyl-4,7,10,13-tetraoxo-3-oxa-5,8,11,14-tetraazahexadecan-16-oate；Boc-(Gly)4-OBn；{2-[2-(2-tert-butoxycarbonylamino-acetylamino)-acetylamiono]-acetylamino}-acetic acid benzyl ester；Boc-Gly-Gly-Gly-Gly-OBn；benzyl 2-[[2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]acetyl]amino]acetate
• CAS: 108432-90-2
• 化学式: C₂₀H₂₈N₄O₇
• 分子量: 436.465
• InChiKey: VGVOUQMBYWKJIM-UHFFFAOYSA-N

物化性质

• 熔点：
  189-190 °C
• 沸点：
  750.1±60.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-GGGG-OCH2Ph 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 5.0~20.0 ℃ 、413.68 kPa 条件下， 反应 76.0h， 生成 2-[[2-[[2-[[2-[[2-[2-(dioctadecylamino)-2-oxoethoxy]acetyl]amino]acetyl]amino]acetyl]amino]acetyl]amino]acetic acid
  参考文献：
  名称：

  Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution

  摘要：

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.

  DOI：

  10.1021/ja0558894
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)glycylglycine benzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 Boc-GGGG-OCH2Ph
  参考文献：
  名称：

  Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine

  摘要：

  在固态下对Boc–Glyn–OBzl（n=3–7）和Boc–(β-Ala)n–OBzl（n=3–8）进行了红外光谱构象分析，结果表明较高聚体（n=5–8）中存在β-折叠结构。溶解度数据显示，Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl在高度极性溶剂中的不溶性分别从六肽和七肽水平开始。保护性同聚肽Gly和β-Ala的不溶性估计是由β-折叠聚集引起的。Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl（n≥5）形成β-折叠结构的高潜力可以明显归因于β-折叠结构中每个Gly和β-Ala残基肽骨架二面角的大自由度。还讨论了蛋白质表面区域中少量Gly残基被β-Ala残基替代的意义。

  DOI：

  10.1246/bcsj.59.3553

文献信息

• Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: Impending synergistic agents
  作者：Sudhir N. Bavikar、Deepak B. Salunke、Braja G. Hazra、Vandana S. Pore、Robert H. Dodd、Josiane Thierry、Fazal Shirazi、Mukund V. Deshpande、Sreenath Kadreppa、Samit Chattopadhyay

  DOI：10.1016/j.bmcl.2008.09.013

  日期：2008.10

  Tetrapeptides derived from glycine and beta-alanine were hooked at the C-3 beta position of the modified cholic acid to realize novel linear tetrapeptide-linked cholic acid derivatives. All the synthesized compounds were tested against a wide variety of microorganisms (Gram-negative bacteria, Gram-positive bacteria and fungi) and their cytotoxicity was evaluated against human embryonic kidney (HEK293) and human mammary adenocarcinoma (MCF-7) cell lines. While relatively inactive by themselves, these compounds interact synergistically with antibiotics such as fluconazole and erythromycin to inhibit growth of fungi and bacteria, respectively, at 1-24 mu g/mL. The synergistic effect shown by our novel compounds is due to their inherent amphiphilicity. The fractional inhibitory concentrations reported are comparable to those reported for Polymyxin B derivatives. (c) 2008 Elsevier Ltd. All rights reserved.
• [EN] ANTI-GLP1R ANTIBODY-DRUG CONJUGATES COMPRISING GLP1 PEPTIDOMIMETICS AND USES THEREOF<br/>[FR] CONJUGUÉS ANTICORPS-MÉDICAMENT ANTI-GLP1R COMPRENANT DES PEPTIDOMIMÉTIQUES DE GLP1 ET LEURS UTILISATIONS
  申请人：[en]REGENERON PHARMACEUTICALS, INC.

  公开号：WO2023173132A1

  公开（公告）日：2023-09-14

  The present invention provides antibody-tethered drug conjugates (ATDCs) and compositions thereof that are useful, for example, for targeting glucagon-like peptide 1 receptor (GLP1 R) and treating various conditions, e.g., diabetes. Methods for making such ATDCs are also provided along with method of use thereof.
• Cation Dependence of Chloride Ion Complexation by Open-Chained Receptor Molecules in Chloroform Solution
  作者：Robert Pajewski、Riccardo Ferdani、Jolanta Pajewska、Ruiqiong Li、George W. Gokel

  DOI：10.1021/ja0558894

  日期：2005.12.1

  Seventeen peptides, most having the sequence GGGPGGG, but differing in the C- and N-terminal ends, have been studied as anion-complexing agents. These relatively simple, open-chained peptide systems interact with both chloride and the associated cation. Changes, in the N- and C-terminal side chains appear to make little difference in the efficacy of binding. NMR studies suggest that the primary interactions involve amide NH contacts with the chloride anion, and CD spectral analyses suggest a concomitant conformational change upon binding. Changes in binding constants, which are expected in different solvents, also suggest selective solvent interactions with the unbound host that helps to preorganize the open-chained peptide system. Significant differences are apparent in complexation strengths when the heptapeptide chain is shortened or lengthened or when the relative position of proline within the heptapeptide is varied.
• Conformations in the Solid State and Solubility Properties of Protected Homooligopeptides of Glycine and β-Alanine
  作者：Mitsuaki Narita、Masamitsu Doi、Koji Kudo、Yusuke Terauchi

  DOI：10.1246/bcsj.59.3553

  日期：1986.11

  IR spectroscopic conformational analyses of Boc–Glyn–OBzl (n=3–7) and Boc–(β-Ala)n–OBzl (n=3–8) were performed in the solid state, suggesting the occurrence of the β-sheet structure in the higher oligomers (n=5–8). Solubility data indicate that insolubilities of Boc–Glyn–OBzl and Boc–(β-Ala)n–OBzl in high-polar solvents begin at hexa- and heptapeptide levels, respectively. Insolubility of protected homooligopeptides of Gly and β-Ala was estimated to be caused by β-sheet aggregation. The high potential for the β-sheet formation of Boc–Glyn–OBzl and Boc–(β-Ala)n–OBzl (n≥5) could clearly be attributed to the great freedom of the peptide backbone dihedral angles of each of the Gly and β-Ala residues in the β-sheet structure. The implications of a replacement of a few Gly residues with β-Ala residues in surface regions of proteins are also discussed.

  在固态下对Boc–Glyn–OBzl（n=3–7）和Boc–(β-Ala)n–OBzl（n=3–8）进行了红外光谱构象分析，结果表明较高聚体（n=5–8）中存在β-折叠结构。溶解度数据显示，Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl在高度极性溶剂中的不溶性分别从六肽和七肽水平开始。保护性同聚肽Gly和β-Ala的不溶性估计是由β-折叠聚集引起的。Boc–Glyn–OBzl和Boc–(β-Ala)n–OBzl（n≥5）形成β-折叠结构的高潜力可以明显归因于β-折叠结构中每个Gly和β-Ala残基肽骨架二面角的大自由度。还讨论了蛋白质表面区域中少量Gly残基被β-Ala残基替代的意义。