Fmoc-His-Pro-Ile-Arg-Ala-Cys-Pro-OCH2CONH2 | 926661-67-8

• 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: Fmoc-His-Pro-Ile-Arg-Ala-Cys-Pro-OCH2CONH2
• CAS: 926661-67-8
• 化学式: C₅₁H₆₉N₁₃O₁₁S
• 分子量: 1072.26
• InChiKey: VYFJTKSRRXLAER-YLRRKRQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.07
• 重原子数：
  76.0
• 可旋转键数：
  25.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  355.32
• 氢给体数：
  11.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  H-Cys-Asp-Ile-Leu-Leu-Gly-NH2 、 Fmoc-His-Pro-Ile-Arg-Ala-Cys-Pro-OCH2CONH2 在 3,3,3-膦三基三丙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到Fmoc-His-Pro-Ile-Arg-Ala-Cys-Asp-Ile-Leu-Leu-Gly-NH2
  参考文献：
  名称：

  The use of a cysteinyl prolyl ester (CPE) autoactivating unit in peptide ligation reactions

  摘要：

  A peptide containing a cysteinyl prolyl ester (CPE) moiety at the C-terminus (CPE peptide) is spontaneously transformed into a diketopiperazine thioester via an intramolecular N-S acyl shift reaction, Followed by diketopiperazine Formation. The CPE peptide can be ligated with a Cys-peptide in a one-pot procedure. The peptide diketopiperazine thioester call also be transformed into a peptide thioester by intermolecular thiol-thioester exchange with external thiol compounds such as sodium mercaptoethanesulfonate. Since CPE peptides call be prepared by standard Fmoc solid-phase synthesis, it is a versatile alternative to the peptide thioester, providing a flexible ligation strategy that promises to be useful in polypeptide synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.008
• 作为产物：
  描述：

  Fmoc-Ala-Cys(Trt)-OH 、 羟基乙酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-异亮氨酸 、 NΑ-FMOC-NΩ-(2,2,5,7,8-五甲基苯并二氢吡喃-6-磺酰基)-L-精氨酸 、 N-Fmoc-N'-三苯甲基-L-组氨酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以22%的产率得到Fmoc-His-Pro-Ile-Arg-Ala-Cys-Pro-OCH2CONH2
  参考文献：
  名称：

  The use of a cysteinyl prolyl ester (CPE) autoactivating unit in peptide ligation reactions

  摘要：

  A peptide containing a cysteinyl prolyl ester (CPE) moiety at the C-terminus (CPE peptide) is spontaneously transformed into a diketopiperazine thioester via an intramolecular N-S acyl shift reaction, Followed by diketopiperazine Formation. The CPE peptide can be ligated with a Cys-peptide in a one-pot procedure. The peptide diketopiperazine thioester call also be transformed into a peptide thioester by intermolecular thiol-thioester exchange with external thiol compounds such as sodium mercaptoethanesulfonate. Since CPE peptides call be prepared by standard Fmoc solid-phase synthesis, it is a versatile alternative to the peptide thioester, providing a flexible ligation strategy that promises to be useful in polypeptide synthesis. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.008

文献信息

• Peptide Ligation Using a Building Block Having a Cysteinyl Prolyl Ester (CPE) Autoactivating Unit at the Carboxy Terminus
  作者：Toru Kawakami、Saburo Aimoto

  DOI：10.1246/cl.2007.76

  日期：2007.1

  CPE peptide ligation using a building block containing a cysteinyl prolyl ester (CPE) autoactivating unit is described. The peptide building block can be prepared by a standard Fmoc chemistry and used in thiol-mediated ligation, such as native chemical ligation.

  本文介绍了使用含有半胱氨酰脯氨酸酯（CPE）自激活单元的结构单元进行 CPE 肽连接的方法。该肽结构单元可通过标准的 Fmoc 化学方法制备，并用于巯基介导的连接，如原生化学连接。