Boc-Ala-Phe-Gly-OH | 1003593-20-1

• 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: Boc-Ala-Phe-Gly-OH
• 英文别名: 2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-phenylpropanoyl]amino]acetic acid
• CAS: 1003593-20-1
• 化学式: C₁₉H₂₇N₃O₆
• 分子量: 393.44
• InChiKey: BNHLBJXRGOUOCN-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Phe-Gly-OH 在 哌啶 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 Boc-Ala-Phe-Gly-Ala-SH
  参考文献：
  名称：

  Promising General Solution to the Problem of Ligating Peptides and Glycopeptides

  摘要：

  Our global goal is that of synthesizing complex polypeptides and glycopeptides in homogeneous form. Chemistry-derived access to homogeneous biologics could well have useful consequences in the discovery of drugs and vaccines. The key finding in this study is that thio acids can become highly competent acyl donors following even trace levels of oxidative activation, thereby undergoing amide bond formation upon reaction with N-terminal peptides. Though our data set does not establish the specific mechanism of this reaction, a framework to account for the fact that minute levels of oxidation actuate amide bond formation with high turnover is offered. An apparently general coupling of thio acids (including complex peptide thio acids with N-termini of complex peptides) has thus been realized. These ligations are conducted with minimal alpha-epimerization in the C-terminal group and allow for the coupling of N-terminal and C-terminal glycopeptides en route to homogeneous glycoproteins.

  DOI：

  10.1021/ja1084628
• 作为产物：
  描述：

  (S)-2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)-3-phenylpropanoic acid 在 水 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 14.0h， 生成 Boc-Ala-Phe-Gly-OH
  参考文献：
  名称：

  氢键替代稳定的水溶性3 10螺旋，其来自含有编码α-氨基酸的无序五肽

  摘要：

  更换假想I + 3→1肽H-键无序五肽，即缺乏任何helicogenicÇ α -tetrasubstituted残基，具有丙基接头和氨甲酰化的N末端氮约束它在难以捉摸3 10具有高螺旋结构通过NMR和CD分析证实了在温度和pH值变化的条件下的螺旋度和稳定性。

  DOI：

  10.1016/j.tetlet.2018.05.029

文献信息

• Gram‐Scale Synthesis of a Hexapeptide by Fragment Coupling in a Ball Mill
  作者：Yves Yeboue、Nadia Rguioueg、Gilles Subra、Jean Martinez、Frédéric Lamaty、Thomas‐Xavier Métro

  DOI：10.1002/ejoc.202100839

  日期：2022.6.7

  using solvent-less techniques such as ball milling, a hexapeptide was synthesized in gram scale without using any toxic solvents. To date, this hexapeptide is the largest precisely controlled amino acid sequence ever synthesized in a ball mill. This study paves the way to future developments for the synthesis of longer peptides (and proteins) by using ball milling.

  通过使用无溶剂技术（如球磨），在不使用任何有毒溶剂的情况下以克级合成六肽。迄今为止，这种六肽是在球磨机中合成的最大的精确控制的氨基酸序列。这项研究为通过使用球磨合成更长的肽（和蛋白质）的未来发展铺平了道路。
• Reversible switching of substrate activity of poly-N-isopropylacrylamide peptide conjugates
  作者：Kian Molawi、Armido Studer

  DOI：10.1039/b713083j

  日期：——

  The activity of smart polymer peptide conjugates towards chymotrypsin catalyzed hydrolysis was reversibly switched on and off using temperature as the trigger.

  智能聚合物肽偶合物对胰凝乳蛋白酶催化水解的活性，通过温度作为触发器实现了可逆的开关控制。
• Promising General Solution to the Problem of Ligating Peptides and Glycopeptides
  作者：Ping Wang、Samuel J. Danishefsky

  DOI：10.1021/ja1084628

  日期：2010.12.1

  Our global goal is that of synthesizing complex polypeptides and glycopeptides in homogeneous form. Chemistry-derived access to homogeneous biologics could well have useful consequences in the discovery of drugs and vaccines. The key finding in this study is that thio acids can become highly competent acyl donors following even trace levels of oxidative activation, thereby undergoing amide bond formation upon reaction with N-terminal peptides. Though our data set does not establish the specific mechanism of this reaction, a framework to account for the fact that minute levels of oxidation actuate amide bond formation with high turnover is offered. An apparently general coupling of thio acids (including complex peptide thio acids with N-termini of complex peptides) has thus been realized. These ligations are conducted with minimal alpha-epimerization in the C-terminal group and allow for the coupling of N-terminal and C-terminal glycopeptides en route to homogeneous glycoproteins.
• Hydrogen bond surrogate stabilized water soluble 310-helix from a disordered pentapeptide containing coded α-amino acids
  作者：Sunit Pal、Erode N. Prabhakaran

  DOI：10.1016/j.tetlet.2018.05.029

  日期：2018.6

  Replacing a hypothetical i + 3 → i peptide H-bond in a disordered pentapeptide, that lacks any helicogenic Cα-tetrasubstituted residues, with a propyl linker and carbamylating the N-terminal nitrogen constrains it in the elusive 310-helical structure with high helicity and stability under varying conditions of temperature and pH, confirmed by NMR and CD analyses.

  更换假想I + 3→1肽H-键无序五肽，即缺乏任何helicogenicÇ α -tetrasubstituted残基，具有丙基接头和氨甲酰化的N末端氮约束它在难以捉摸3 10具有高螺旋结构通过NMR和CD分析证实了在温度和pH值变化的条件下的螺旋度和稳定性。