(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-[[2-(1,2,5-dithiazepan-5-yl)-2-oxoethyl]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 | 1255709-30-8

• 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: (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-[[2-(1,2,5-dithiazepan-5-yl)-2-oxoethyl]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
• CAS: 1255709-30-8
• 化学式: C₄₇H₇₉N₁₃O₁₁S₂
• 分子量: 1066.36
• InChiKey: JIGYGKZMDMVPSJ-SICVRDKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  73
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  413
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (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-[[2-(1,2,5-dithiazepan-5-yl)-2-oxoethyl]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 在 三(2-羰基乙基)磷盐酸盐 、 sodium hydroxide 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  深入了解SEA酰胺硫酯平衡。在中性pH下用于合成硫酯的应用†

  摘要：

  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。

  DOI：

  10.1039/c6ob01079b
• 作为产物：
  描述：

  在 碳酸氢铵 作用下， 以 水 为溶剂， 以81 mg的产率得到(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-[[2-(1,2,5-dithiazepan-5-yl)-2-oxoethyl]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
  参考文献：
  名称：

  Bis(2-sulfanylethyl)amino Native Peptide Ligation

  摘要：

  The reaction of a peptide featuring a bis(2-sulfanylethyl)amino (SEA) group on its C-terminus with a cysteinyl peptide in water at pH 7 and 37 C leads to the chemoselective and regioselective formation of a native peptide bond. This method called SEA ligation enriches the native peptide ligation repertoire available to the peptide chemist. Preparation of an innovative solid support which allows the straightforward synthesis of peptide SEA fragments using standard Fmoc/fert-butyl solid phase peptide synthesis procedures is also described.

  DOI：

  10.1021/ol102273u

文献信息

• 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.
• Selenopeptide Transamidation and Metathesis
  作者：Nathalie Ollivier、Annick Blanpain、Emmanuelle Boll、Laurent Raibaut、Hervé Drobecq、Oleg Melnyk

  DOI：10.1021/ol501866j

  日期：2014.8.1

  Selenopeptides can be transamidated by cysteinyl peptides in water using mild conditions (pH 5.5, 37 °C) in the presence of an arylthiol catalyst. Similar conditions also catalyze the metathesis of selenopeptides. The usefulness of the selenophosphine derived from TCEP (TCEP═Se) for inhibiting the TCEP-induced deselenization of selenocysteine residue is also reported.
• Synthesis of Thiazolidine Thioester Peptides and Acceleration of Native Chemical Ligation
  作者：Julien Dheur、Nathalie Ollivier、Oleg Melnyk

  DOI：10.1021/ol2002804

  日期：2011.3.18

  Thiazolidine thioester peptides were synthesized by reacting bis(2-sulfanylethyl)amido peptides with glyoxylic acid at pH 1. A significant increase in Native Chemical Ligation (NCL) rate was observed with thiazolidine thioesters compared to 3-mercaptopropionic acid-thioester analogues. The method is of particular interest for accelerating valine-cysteine peptide bond formation.