N-allyloxycarbonyl-L-seryl-(O)-diallylphosphato-L-seryl-L-prolyl-glycyl-(O)-diallylphosphato-L-serine allyl ester | 310463-48-0

• 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-allyloxycarbonyl-L-seryl-(O)-diallylphosphato-L-seryl-L-prolyl-glycyl-(O)-diallylphosphato-L-serine allyl ester
• CAS: 310463-48-0
• 化学式: C₃₅H₅₃N₅O₁₇P₂
• 分子量: 877.777
• InChiKey: BRIZUJDZQFCYRR-DZUOILHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  59.0
• 可旋转键数：
  32.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  281.99
• 氢给体数：
  5.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl-L-seryl-(O)-diallylphosphato-L-seryl-L-prolyl-glycyl-(O)-diallylphosphato-L-serine allyl ester 在 四氮唑 、 四(三苯基膦)钯 、 甲酸 、 正丁胺 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (O)-phosphato-L-seryl-(O)-phosphato-L-seryl-L-prolyl-glycyl-(O)-phosphato-L-serine
  参考文献：
  名称：

  Synthesis of a triply phosphorylated pentapeptide from human τ-protein

  摘要：

  Two different strategies for the synthesis of a triply phosphorylated pentapeptide are described. In both cases a monophosphorylated selectively N-deprotected tripeptide is employed as C-terminal fragment. Coupling of this building block with a C-terminally unmasked bis-phosphorylated seryl-dipeptide unexpectedly failed due to decomposition of this peptide upon activation with different coupling reagents. Instead stepwise N-terminal elongation of the peptide chain with serine derivatives and subsequent O-phosphorylation of the serine OH-groups was successful. These results indicate that assembly of multiply phosphorylated peptides from preformed multiply phosphorylated phosphopeptide building blocks in general may be problematic and that a stepwise elongation of the amino acid chain may be preferable. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00174-7
• 作为产物：
  描述：

  Alloc-Ser-OH 、 (O)-diallylphosphato-L-seryl-L-prolyl-glycyl-(O)-diallylphosphato-L-serine allyl ester trifluoroacetate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到N-allyloxycarbonyl-L-seryl-(O)-diallylphosphato-L-seryl-L-prolyl-glycyl-(O)-diallylphosphato-L-serine allyl ester
  参考文献：
  名称：

  Synthesis of a triply phosphorylated pentapeptide from human τ-protein

  摘要：

  Two different strategies for the synthesis of a triply phosphorylated pentapeptide are described. In both cases a monophosphorylated selectively N-deprotected tripeptide is employed as C-terminal fragment. Coupling of this building block with a C-terminally unmasked bis-phosphorylated seryl-dipeptide unexpectedly failed due to decomposition of this peptide upon activation with different coupling reagents. Instead stepwise N-terminal elongation of the peptide chain with serine derivatives and subsequent O-phosphorylation of the serine OH-groups was successful. These results indicate that assembly of multiply phosphorylated peptides from preformed multiply phosphorylated phosphopeptide building blocks in general may be problematic and that a stepwise elongation of the amino acid chain may be preferable. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00174-7