(S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-2-enoic acid | 170168-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-2-enoic acid
• 英文别名: (S,E)-4-((Fmoc)amino)-pent-2-enoate
• CAS: 170168-60-2
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: INXKJTKVLQXADX-NHAQELONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 Fmoc-L-丙氨酸 、 (S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-2-enoic acid 、 Fmoc-Leu-OH 、 Fmoc-L-异亮氨酸 、 三氟乙酸 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.1h， 以53 mg的产率得到IleLeuLeuApaAla
  参考文献：
  名称：

  Synthesis of Gallinamide A Analogues as Potent Falcipain Inhibitors and Antimalarials

  摘要：

  Analogues of the natural product gallinamide A were prepared to elucidate novel inhibitors of the falcipain cysteine proteases. Analogues exhibited potent inhibition of falcipain-2 (FP-2) and falcipain-3 (FP-3) and of the development of Plasmodium falciparum in vitro. Several compounds were equipotent to chloroquine as inhibitors of the 3D7 strain of P. falciparum and maintained potent activity against the chloroquine-resistant Dd2 parasite. These compounds serve as promising leads for the development of novel antimalarial agents.

  DOI：

  10.1021/jm501439w
• 作为产物：
  描述：

  (2E,4s)-4-[[(1,1-二甲基乙氧基)羰基]氨基]-2-戊烯酸 在 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 (S,E)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-2-enoic acid
  参考文献：
  名称：

  Self-Assembly to Function: Design, Synthesis, and Broad Spectrum Antimicrobial Properties of Short Hybrid E-Vinylogous Lipopeptides

  摘要：

  Nonribosomal E-vinylogous gamma-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating alpha-and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the alpha-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.

  DOI：

  10.1021/jm400884w