prop-2-enyl 4-[[(2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]amino]butanoate | 1026641-38-2

• 分子结构分类: 有机化合物
• 英文名称: prop-2-enyl 4-[[(2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]amino]butanoate
• CAS: 1026641-38-2
• 化学式: C₂₈H₃₅N₃O₅
• 分子量: 493.603
• InChiKey: DIKPAKSVURXZQN-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 4-(芴甲氧羰基氨基)丁酸 、 prop-2-enyl 4-[[(2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]amino]butanoate 以0.138 g的产率得到(3S,11S,19S,27S,35S)-3,11,19,27,35-pentakis(4-aminobutyl)-1,4,9,12,17,20,25,28,33,36-decazacyclotetracontane-2,5,10,13,18,21,26,29,34,37-decone
  参考文献：
  名称：

  Large Cyclic Peptides as Cores of Multivalent Ligands:  Application to Inhibitors of Receptor Binding by Cholera Toxin

  摘要：

  Large cyclic decapeptides (up to 50-atom ring) were synthesized efficiently on the solid phase with allyl-ester protection of the carboxyl terminus during elongation. Pentavalent ligands, in a "core-linker-finger" modular setup, were assembled by using these cyclic peptide cores to demonstrate large affinity gains for inhibition of surface receptor binding by the cholera toxin B pentamer. The results suggest that the peptide cores retain expanded conformation in solution so that shorter flexible linkers are needed for larger peptide cores to achieve the best inhibitory results.

  DOI：

  10.1021/jo0489770
• 作为产物：
  描述：

  allyl 4-aminobutanoate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 prop-2-enyl 4-[[(2S)-6-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoyl]amino]butanoate
  参考文献：
  名称：

  Large Cyclic Peptides as Cores of Multivalent Ligands:  Application to Inhibitors of Receptor Binding by Cholera Toxin

  摘要：

  Large cyclic decapeptides (up to 50-atom ring) were synthesized efficiently on the solid phase with allyl-ester protection of the carboxyl terminus during elongation. Pentavalent ligands, in a "core-linker-finger" modular setup, were assembled by using these cyclic peptide cores to demonstrate large affinity gains for inhibition of surface receptor binding by the cholera toxin B pentamer. The results suggest that the peptide cores retain expanded conformation in solution so that shorter flexible linkers are needed for larger peptide cores to achieve the best inhibitory results.

  DOI：

  10.1021/jo0489770