Fmoc-Amp(Alloc)-OH | 1000787-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Amp(Alloc)-OH
• 英文别名: (2S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-1-prop-2-enoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 1000787-42-7
• 化学式: C₂₄H₂₄N₂O₆
• 分子量: 436.464
• InChiKey: IKAPJKQKVHYVSL-BTYIYWSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105.17
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Rink amide resin 、 Fmoc-Amp(Alloc)-OH 、 苯乙醛 、 异戊醛 、 N-Boc-顺式-4-Fmoc-氨基-L-脯氨酸 、 [2-[2-(Fmoc-氨基)乙氧基]乙氧基]乙酸 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4S)-4-amino-N-[(3S,5S)-5-[[(3S,5S)-5-[[(3S,5S)-5-[[(3S,5S)-5-[[(3S,5S)-5-[2-[2-[2-[2-[2-(2-amino-2-oxoethoxy)ethoxy]ethylamino]-2-oxoethoxy]ethoxy]ethylcarbamoyl]-1-(2-phenylethyl)pyrrolidin-3-yl]carbamoyl]-1-(3-methylbutyl)pyrrolidin-3-yl]carbamoyl]-1-(2-phenylethyl)pyrrolidin-3-yl]carbamoyl]-1-(3-methylbutyl)pyrrolidin-3-yl]carbamoyl]-1-(2-phenylethyl)pyrrolidin-3-yl]-1-(3-methylbutyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Cell-penetrating γ-peptide/antimicrobial undecapeptide conjugates with anticancer activity

  摘要：

  In this study, we combined a cell-penetrating gamma-peptide, PEG-1, with antimicrobial undecapeptides in order to provide compounds with anticancer properties against MDA-MB-231 human breast cancer cells. We demonstrated that the conjugates were more cytotoxic than Ac-PEG-1 and the parent undecapeptides. We also evaluated the toxicity of the conjugates against non-malignant cells. The peptide conjugate with the best biological profile was BP77-PEG-1, which, at 10 mu M, showed a 71% growth inhibition in MDA-MB-231 cells and only a 17% inhibition in non-malignant cells. Therefore, this study suggests that PEG-1 mediated the undecapeptide delivery into cancer cells and that these conjugates are the proof-of-concept of this strategy to generate improved anticancer drugs based on peptides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.003