N-tert-butyloxycarbonyl-glycyl-glycyl-(S-palmitoyl)-L-cysteine | 207398-62-7

• 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
• 英文名称: N-tert-butyloxycarbonyl-glycyl-glycyl-(S-palmitoyl)-L-cysteine
• 英文别名: Boc-Gly-Gly-Cys(palmitoyl)(palmitoyl)-OH；(2R)-3-hexadecanoylsulfanyl-2-[[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]acetyl]amino]propanoic acid
• CAS: 207398-62-7
• 化学式: C₂₈H₅₁N₃O₇S
• 分子量: 573.795
• InChiKey: HHNBJBKFNOMULT-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  176
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-glycyl-glycyl-(S-palmitoyl)-L-cysteine 在 四(三苯基膦)钯 1,3-二甲基巴比妥酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-tert-butyloxycarbonyl-glycyl-glycyl-(S-palmitoyl)-L-cysteyl-L-prolyl-(S-geranylgeranyl)-L-cycteine methyl ester
  参考文献：
  名称：

  Synthesis of characteristic lipopeptides of lipid modified proteins employing the allyl ester as protecting group

  摘要：

  在非常温和的条件下，通过选择性 Pd0 介导的烯丙基酯去除作为关键步骤，有效地构建了代表脂质化人类 GαO 蛋白、人类 N- 和 R-Ras 蛋白脂质化修饰亚结构的脂质化肽。

  DOI：

  10.1039/a708749g
• 作为产物：
  描述：

  Boc-甘氨酰甘氨酸 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 、 DL-dithiothreitol 、 1-羟基苯并三唑 、 达卡巴嗪 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N-tert-butyloxycarbonyl-glycyl-glycyl-(S-palmitoyl)-L-cysteine
  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

文献信息

• Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins
  作者：T. Schmittberger、H. Waldmann

  DOI：10.1016/s0968-0896(98)00251-x

  日期：1999.5

  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.
• Synthesis of characteristic lipopeptides of lipid modified proteins employing the allyl ester as protecting group
  作者：Thierry Schmittberger、Alain Cotté

  DOI：10.1039/a708749g

  日期：——

  Lipidated peptides which represent characteristic lipid modified substructures of lipidated human GαO protein and the human N- and R-Ras proteins were built up efficiently by employing the selective Pd0-mediated removal of allyl esters under very mild conditions as the key step.

  在非常温和的条件下，通过选择性 Pd0 介导的烯丙基酯去除作为关键步骤，有效地构建了代表脂质化人类 GαO 蛋白、人类 N- 和 R-Ras 蛋白脂质化修饰亚结构的脂质化肽。