| 1280612-48-7

• 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
• CAS: 1280612-48-7
• 化学式: C₄₇H₈₁N₁₃O₁₁S₂
• 分子量: 1068.37
• InChiKey: ZLXZNXLAEXDCNH-SICVRDKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  73.0
• 可旋转键数：
  35.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  371.13
• 氢给体数：
  13.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  、 乙醛酸 在 三氟乙酸 作用下， 以 水 为溶剂， 以10.8 mg的产率得到3-((3S,6S)-6-((1H-imidazol-4-yl)methyl)-1-((S)-1-(L-isoleucyl-L-leucyl-L-lysyl-L-glutamyl)pyrrolidin-2-yl)-3-isopropyl-1,4,7,10,13-pentaoxo-14-thia-2,5,8,11-tetraazahexadecan-16-yl)thiazolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Thiazolidine Thioester Peptides and Acceleration of Native Chemical Ligation

  摘要：

  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.

  DOI：

  10.1021/ol2002804
• 作为产物：
  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 三氟乙酸 、 锌 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Thiazolidine Thioester Peptides and Acceleration of Native Chemical Ligation

  摘要：

  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.

  DOI：

  10.1021/ol2002804

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.