H-ILKEPVHGA-SCH₂CH₂CO₂H

• 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: H-ILKEPVHGA-SCH₂CH₂CO₂H
• 英文别名: ILKEPVHGA-S(CH2)2COOH；(4S)-4-[[(2S)-6-amino-2-[[(2S)-2-[[(2S,3S)-2-amino-3-methylpentanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]amino]-5-[(2S)-2-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-(2-carboxyethylsulfanyl)-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamoyl]pyrrolidin-1-yl]-5-oxopentanoic acid
• 化学式: C₄₇H₇₈N₁₂O₁₃S
• 分子量: 1051.27
• InChiKey: QXEHYMUYKPQCBA-ALQOTQCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  73
• 可旋转键数：
  34
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  422
• 氢给体数：
  12
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  H-ILKEPVHGA-SCH₂CH₂CO₂H 、 在 3,3,3-膦三基三丙酸 、 4-巯基苯基乙酸 、 盐酸胍 作用下， 以 aq. phosphate buffer 为溶剂， 以75 %的产率得到
  参考文献：
  名称：

  Incorporation of a Highly Reactive Oxalyl Thioester-Based Interacting Handle into Proteins

  摘要：

  DOI：

  10.1021/acs.orglett.3c01846
• 作为产物：
  描述：

  ILKEPVHGA-SEA^off 在 3,3,3-膦三基三丙酸 、 3-巯基丙酸 作用下， 生成 H-ILKEPVHGA-SCH₂CH₂CO₂H
  参考文献：
  名称：

  Incorporation of a Highly Reactive Oxalyl Thioester-Based Interacting Handle into Proteins

  摘要：

  DOI：

  10.1021/acs.orglett.3c01846

文献信息

• Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates
  作者：Laurent Raibaut、Marine Cargoët、Nathalie Ollivier、Yun Min Chang、Hervé Drobecq、Emmanuelle Boll、Rémi Desmet、Jean-Christophe M. Monbaliu、Oleg Melnyk

  DOI：10.1039/c5sc03459k

  日期：——

  SeEA latent selenoester: go fast by switching to selenium.

  SeEA 潜在硒酯：通过改用硒来加快速度。
• Insight into the SEA amide thioester equilibrium. Application to the synthesis of thioesters at neutral pH
  作者：S. L. Pira、O. El Mahdi、L. Raibaut、H. Drobecq、J. Dheur、E. Boll、O. Melnyk

  DOI：10.1039/c6ob01079b

  日期：——

  bis(2-sulfanylethyl)amide (SEA) N,S-acyl shift thioester surrogate has found a variety of useful applications in the field of protein total synthesis. Here we present novel insights into the SEA amide/thioester equilibrium in water which is an essential step in any reaction involving the thioester surrogate properties of the SEA group. We also show that the SEA amide thioester equilibrium can be efficiently displaced

  的双（2-硫烷基乙基）酰胺（SEA）Ñ，小号酰基蛋白质总合成领域的各种有用的应用转移硫酯替代发现了。在这里，我们介绍了水中SEA酰胺/硫酯平衡的新颖见解，这是任何涉及SEA组硫酯替代性质的反应中必不可少的步骤。我们还表明，SEA酰胺硫代酸酯平衡可以在中性pH下有效地置换，以获取肽烷基硫代酸酯，即天然化学连接（NCL）反应的关键组分。
• Synthesis of Peptide Alkylthioesters Using the Intramolecular <i>N</i>,<i>S</i>-Acyl Shift Properties of Bis(2-sulfanylethyl)amido Peptides
  作者：Julien Dheur、Nathalie Ollivier、Aurélie Vallin、Oleg Melnyk

  DOI：10.1021/jo200029e

  日期：2011.5.6

  The design of novel methods giving access to peptide alkylthioesters, the key building blocks for protein synthesis using Native Chemical Ligation, is an important area of research. Bis(2-sulfanylethyl)amido peptides (SEA peptides) 1 equilibrate in aqueous solution with S-2-(2-mercaptoethylamino)ethyl thioester peptides 2 through an N,S-acyl shift mechanism. HPLC was used to study the rate of equilibration for different C-terminal amino acids and the position of equilibrium as a function of pH. We show also that thioester form 2 can participate efficiently in a thiol-thioester exchange reaction with 5% aqueous 3-mercaptopropionic acid. The highest reaction rate was obtained at pH 4. These experimental conditions are significantly less acidic than those reported in the past for related systems. The method was validated with the synthesis of a 24-mer peptide thioester. Consequently, SEA peptides 1 constitute a powerful platform for access to native chemical ligation methodologies.
• Bis(2-sulfanylethyl)amido Peptides Enable Native Chemical Ligation at Proline and Minimize Deletion Side-Product Formation
  作者：Laurent Raibaut、Phillip Seeberger、Oleg Melnyk

  DOI：10.1021/ol402678a

  日期：2013.11

  Native chemical ligation of C-terminal peptidyl prolyl alkylthioesters with N-terminal cysteinyl peptides usually exhibits poor kinetic rates compared to other C-terminal amino acid residues. It is shown here that the reaction is accompanied by the formation of a deletion side product which is minimized by using a bis(2-sulfanylethyl)amido (SEA) thioester surrogate at a mildly acidic pH.
• Incorporation of a Highly Reactive Oxalyl Thioester-Based Interacting Handle into Proteins
  作者：Benjamin Grain、Rémi Desmet、Benoît Snella、Oleg Melnyk、Vangelis Agouridas

  DOI：10.1021/acs.orglett.3c01846

  日期：2023.7.14