trityl-Gly-Cys(palmitoyl)-Met-Gly-Leu-Pro-Cys(farnesyl) | 608133-86-4

• 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: trityl-Gly-Cys(palmitoyl)-Met-Gly-Leu-Pro-Cys(farnesyl)
• 英文别名: Trt-Gly-Cys(Pal)-Met-Gly-Leu-Pro-Cys(Far)-OMe
• CAS: 608133-86-4
• 化学式: C₇₇H₁₁₅N₇O₉S₃
• 分子量: 1379.0
• InChiKey: ZBHNMEUEYALHGC-PJCCTPDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.48
• 重原子数：
  96.0
• 可旋转键数：
  48.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  221.21
• 氢给体数：
  6.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  trityl-Gly-Cys(palmitoyl)-Met-Gly-Leu-Pro-Cys(farnesyl) 在 溶剂黄146 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 生成 Gly-Cys(palmitoyl)-Met-Gly-Leu-Pro-Cys(farnesyl)
  参考文献：
  名称：

  Partitioning of Dual-Lipidated Peptides into Membrane Microdomains:  Lipid Sorting vs Peptide Aggregation

  摘要：

  The lateral membrane organization and phase behavior of the lipid mixture DMPC(di-C-14)/DSPC(di-C-18)/cholesterol (0-33 mol %) with and without an incorporated fluorescence-labeled palmitoyl/farnesyl dual-lipidated peptide, BODIPY-Gly-Cys(Pal)-Met-Gly-Leu-Pro-Cys(Far)-OMe, which represents a membrane recognition model system for Ras proteins, was studied by two-photon excitation fluorescence microscopy. Measurements were performed on giant unilamellar vesicles (GUVs) over a large temperature range, ranging from 30 to 80 degreesC to cover different lipid phase states (all-gel, fluid/gel, liquid-ordered, all-fluid). At temperatures where the fluid-gel coexistence region of the pure binary phospholipid system occurs, large-scale concentration fluctuations appear. Incorporation of cholesterol levels up to 33 mol % leads to a significant increase of conformational order in the membrane system and a reduction of large domain structures. Adding the peptide leads to dramatic changes in the lateral organization of the membrane. With cholesterol present, a phase separation is induced by a lipid sorting mechanism owing to the high affinity of the lipidated peptide to a fluid, DMPC-rich environment. This phase separation leads to the formation of peptide-containing domains with high fluorescence intensity that become progressively smaller with decreasing temperature. As a result, the local concentration of the peptide increases steadily within the confines of the shrinking domains. At the lowest temperatures, where the acyl-chain order parameter of the membrane has already drastically increased and the membrane achieves a liquid-ordered character, an efficient lipid sorting mechanism is no longer supported and aggregation of the peptide into small clusters prevails. We can conclude that palmitoyl/farnesyl dual-lipidated peptides do not associate with liquid-ordered or gel-like domains in phase-separated bilayer membranes. In particular, the study shows the interesting ability of the peptide to induce formation of fluid microdomains at physiologically relevant cholesterol concentrations, and this effect very much depends on the concentration of fluid vs ordered lipid molecules.

  DOI：

  10.1021/ja049922i
• 作为产物：
  描述：

  甲醇 、 N-(三苯甲基)甘氨酸 、 Fmoc-甘氨酸 、 Fmoc-L-蛋氨酸 、 Fmoc-S-(4-甲氧基三苯甲基)-L-半胱氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 、 alkaline earth salt of/the/ methylsulfuric acid 以68%的产率得到trityl-Gly-Cys(palmitoyl)-Met-Gly-Leu-Pro-Cys(farnesyl)
  参考文献：
  名称：

  在固体支持物上酸和碱不稳定的脂肽的合成。

  摘要：

  通过一种新的固相技术，以22-68％的产率合成了包括人Ras蛋白特征部分结构在内的脂化肽。该技术使法尼基化，棕榈酰化和双脂化的肽成为带有荧光标签或马来酰亚胺部分的甲酯或羧酸，可与蛋白质偶联。通过使用9-芴基甲氧基羰基化学以及可氧化裂解的酰肼连接基，在树脂上建立肽主链。作为关键步骤，在从半胱氨酸残基上切割适当的酸敏感或还原敏感的保护基之后，将酸不稳定的法呢基和碱性不稳定的棕榈酰基脂质基团引入树脂。任选地将不同的荧光标签或马来酰亚胺基团引入肽中，然后通过在弱酸性或碱性介质中的非常温和的铜（II）介导的氧化，释放作为甲基酯或羧酸的树脂结合的目标肽。这种新的方法学应该大大促进脂化肽的获得，以研究重要的生物学现象，例如生物信号转导，定位和囊泡运输。

  DOI：

  10.1002/chem.200304822