N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-proline allyl ester | 236425-07-3

• 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: N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-proline allyl ester
• CAS: 236425-07-3
• 化学式: C₄₈H₇₈N₆O₁₀S
• 分子量: 931.248
• InChiKey: KGRZUNCSKWUKMN-GTKRZRNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  65.0
• 可旋转键数：
  31.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  229.41
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl S-farnesylcysteine 、 N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-proline allyl ester 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以53%的产率得到N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-prolyl-(S-farnesyl)-L-cysteine methyl ester
  参考文献：
  名称：

  Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

  摘要：

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00251-x
• 作为产物：
  描述：

  N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-proline allyl ester 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以69%的产率得到N-tert-butyloxycarbonyl-glycyl-(S-palmitoyl)-L-cysteyl-L-phenylalanyl-glycine-L-leucyl-L-proline allyl ester
  参考文献：
  名称：

  Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

  摘要：

  For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00251-x