Fmoc-(Et)Cys(Trt)-OBt | 1044496-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Fmoc-(Et)Cys(Trt)-OBt
• CAS: 1044496-63-0
• 化学式: C₄₅H₃₈N₄O₄S
• 分子量: 730.887
• InChiKey: DLCONIIULLVSTA-WBCKFURZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  N,N'-双芴甲氧羰基-L-赖氨酸 、 Fmoc-(Et)Cys(Trt)-OBt 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Efficient Sequential Segment Coupling Using N-Alkylcysteine-Assisted Thioesterification for Glycopeptide Dendrimer Synthesis

  摘要：

  A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester 3-mercaptopgropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.

  DOI：

  10.1021/ol801340m
• 作为产物：
  描述：

  在 哌啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.33h， 生成 Fmoc-(Et)Cys(Trt)-OBt
  参考文献：
  名称：

  Efficient Sequential Segment Coupling Using N-Alkylcysteine-Assisted Thioesterification for Glycopeptide Dendrimer Synthesis

  摘要：

  A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted thioesterification. The glycopeptide having C-terminal NAC was prepared by the Fmoc method and converted to the thioester 3-mercaptopgropionic acid treatment. The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, which was then converted to the thioester. Two tetramers were condensed with ethylenediamine to give the octameric glycopeptide dendrimer.

  DOI：

  10.1021/ol801340m

文献信息

• Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
  作者：Hironobu Hojo、Yuichi Murasawa、Hidekazu Katayama、Tsuyoshi Ohira、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1039/b800884a

  日期：——

  Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

  通过改进的N-烷基半胱氨酸(NAC)辅助硫酯化反应，采用传统的9-芴甲氧羰基(Fmoc)策略制备了肽段的芳基硫酯。含有C端NAC的肽段通过Fmoc策略制备，并通过4-巯基苯乙酸(MPAA)处理转化为芳基硫酯，过程中未发生显著的副反应。这种肽硫酯被用于高效制备95个氨基酸的趋化因子CCL27，采用无Ag+的硫酯方法。
• The Mercaptomethyl Group Facilitates an Efficient One-Pot Ligation at Xaa-Ser/Thr for (Glyco)peptide Synthesis
  作者：Hironobu Hojo、Chinatsu Ozawa、Hidekazu Katayama、Akiharu Ueki、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1002/anie.201000384

  日期：——

  Going native: A mercaptomethyl group on the side‐chain hydroxy group of serine and threonine residues facilitates a native chemical ligation reaction at the Xaa‐Ser/Thr site (see scheme; R=H or Me). The intermediate thioester is treated to achieve an S‐ to N‐acyl shift. After ligation, the group is spontaneously removed to obtain the glycopeptide contulakin‐G and human calcitonin.

  天然化：丝氨酸和苏氨酸残基的侧链羟基上的巯基甲基有助于Xaa-Ser / Thr位点的天然化学连接反应（请参阅方案； R = H或Me）。中间体硫酯经过处理，可实现S到N酰基的转变。连接后，自发去除该基团以获得糖肽contulakin-G和人降钙素。