Fmoc-cis-N3-Pro-β-Ala | 1393723-65-3

• 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: Fmoc-cis-N3-Pro-β-Ala
• 英文别名: 3-((2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-azidopyrrolidine-2-carboxamido)propanoic acid
• CAS: 1393723-65-3
• 化学式: C₂₃H₂₃N₅O₅
• 分子量: 449.466
• InChiKey: BFUOIAIAGNTOCX-XOBRGWDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  144.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-乙基-1-戊炔-3-醇 、 Fmoc-cis-N3-Pro-β-Ala 在 3,3,3-膦三基三丙酸 、 碳酸氢钠 、 copper(II) sulfate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 叔丁醇 为溶剂， 生成 3-((2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(4-(3-hydroxypentan-3-yl)-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamido)propanoic acid
  参考文献：
  名称：

  Discovery of Small-Molecule Interleukin-2 Inhibitors from a DNA-Encoded Chemical Library

  摘要：

  AbstractLibraries of chemical compounds individually coupled to encoding DNA tags (DNA‐encoded chemical libraries) hold promise to facilitate exceptionally efficient ligand discovery. We constructed a high‐quality DNA‐encoded chemical library comprising 30 000 drug‐like compounds; this was screened in 170 different affinity capture experiments. High‐throughput sequencing allowed the evaluation of 120 million DNA codes for a systematic analysis of selection strategies and statistically robust identification of binding molecules. Selections performed against the tumor‐associated antigen carbonic anhydrase IX (CA IX) and the pro‐inflammatory cytokine interleukin‐2 (IL‐2) yielded potent inhibitors with exquisite target specificity. The binding mode of the revealed pharmacophore against IL‐2 was confirmed by molecular docking. Our findings suggest that DNA‐encoded chemical libraries allow the facile identification of drug‐like ligands principally to any protein of choice, including molecules capable of disrupting high‐affinity protein–protein interactions.

  DOI：

  10.1002/chem.201200952