tert-butyl N-[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]amino]-6-[[(2S)-1-[[(2S)-3-methyl-1-[[(2S)-3-methyl-1-[(2S)-2-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-1-[(2S)-2-[[(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxo-1-[3-(prop-2-enoxycarbonylamino)propylamino]propan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-6-oxohexyl]carbamate | 1174139-16-2

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: tert-butyl N-[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]amino]-6-[[(2S)-1-[[(2S)-3-methyl-1-[[(2S)-3-methyl-1-[(2S)-2-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-1-[(2S)-2-[[(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxo-1-[3-(prop-2-enoxycarbonylamino)propylamino]propan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-6-oxohexyl]carbamate
• CAS: 1174139-16-2
• 化学式: C₁₀₀H₁₅₆N₁₈O₂₂
• 分子量: 1962.45
• InChiKey: PKHWGSKFXASBJR-MMZHSJGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  140
• 可旋转键数：
  58
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  549
• 氢给体数：
  16
• 氢受体数：
  23

反应信息

• 作为产物：
  描述：

  tert-butyl N-[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]amino]-6-[[(2S)-1-[[(2S)-3-methyl-1-[[(2S)-3-methyl-1-[(2S)-2-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-1-[(2S)-2-[[(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxo-1-[3-(prop-2-enoxycarbonylamino)propylamino]propan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-6-oxohexyl]carbamate 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以75%的产率得到tert-butyl N-[(5S)-5-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoyl]amino]-6-[[(2S)-1-[[(2S)-3-methyl-1-[[(2S)-3-methyl-1-[(2S)-2-[[2-[[(2S)-1-[[(2S)-1-[[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-1-[(2S)-2-[[(2S)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]-1-oxo-1-[3-(prop-2-enoxycarbonylamino)propylamino]propan-2-yl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamoyl]pyrrolidin-1-yl]-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-6-oxohexyl]carbamate
  参考文献：
  名称：

  On the Emerging Role of Chemistry in the Fashioning of Biologics: Synthesis of a Bidomainal Fucosyl GM1-Based Vaccine for the Treatment of Small Cell Lung Cancer

  摘要：

  The synthesis of the novel small cell lung cancer (SCLC) fucosyl GM1-based vaccine construct, featuring insertion of the HLA-DR binding 15 amino acid sequence derived from Plasmodium falciparum, is described, The resultant glycopeptide has been synthesized in an efficient manner. Finally, successful conjugation of the glycopeptide to the keyhole limpet hemocyanin (KLH) carrier protein completed the preparation of the vaccine.

  DOI：

  10.1021/jo900918m

文献信息

• On the Emerging Role of Chemistry in the Fashioning of Biologics: Synthesis of a Bidomainal Fucosyl GM1-Based Vaccine for the Treatment of Small Cell Lung Cancer
  作者：Pavel Nagorny、Woo Han Kim、Qian Wan、Dongjoo Lee、Samuel J. Danishefsky

  DOI：10.1021/jo900918m

  日期：2009.8.7

  The synthesis of the novel small cell lung cancer (SCLC) fucosyl GM1-based vaccine construct, featuring insertion of the HLA-DR binding 15 amino acid sequence derived from Plasmodium falciparum, is described, The resultant glycopeptide has been synthesized in an efficient manner. Finally, successful conjugation of the glycopeptide to the keyhole limpet hemocyanin (KLH) carrier protein completed the preparation of the vaccine.