2-[(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-oxoazepan-1-yl]acetic acid | 142855-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-oxoazepan-1-yl]acetic acid
• CAS: 142855-53-6
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: ZYSRRJZAOFHCSC-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3(R)-3-amino-2-oxo-1-piperidine-acetic acid 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-[(3R)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-oxoazepan-1-yl]acetic acid
  参考文献：
  名称：

  Structure–activity relationships of a peptide inhibitor of the human FcRn:human IgG interaction

  摘要：

  A family of five peptides was previously discovered by phage display techniques that binds to the human neonatal Fc receptor (FcRn) and inhibits the human IgG: human FcRn protein-protein interaction [Proc. Nat. Acad. Sci. U. S. A. 2008, 105, 2337-2342]. The consensus peptide motif consists of the sequence GHFGGXY where X is preferably a hydrophobic amino acid, and also includes a disul. de bridge enclosing 11-amino acids in varying positions about the consensus sequence. We describe herein the structure activity relationships of one of the five peptides in binding to FcRn using surface plasmon resonance and IgG: FcRn competition ELISA assays. Modi. cations of the peptide length, cyclization, and the incorporation of amino acid substitutions and dipeptide mimetics were studied. The most potent analogs exhibited a 50-to 100-fold improvement of in vitro activity over that of the phage-identified peptide sequence. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.004

文献信息

• Structure–activity relationships of a peptide inhibitor of the human FcRn:human IgG interaction
  作者：Adam R. Mezo、Kevin A. McDonnell、Alfredo Castro、Cara Fraley

  DOI：10.1016/j.bmc.2008.05.004

  日期：2008.6

  A family of five peptides was previously discovered by phage display techniques that binds to the human neonatal Fc receptor (FcRn) and inhibits the human IgG: human FcRn protein-protein interaction [Proc. Nat. Acad. Sci. U. S. A. 2008, 105, 2337-2342]. The consensus peptide motif consists of the sequence GHFGGXY where X is preferably a hydrophobic amino acid, and also includes a disul. de bridge enclosing 11-amino acids in varying positions about the consensus sequence. We describe herein the structure activity relationships of one of the five peptides in binding to FcRn using surface plasmon resonance and IgG: FcRn competition ELISA assays. Modi. cations of the peptide length, cyclization, and the incorporation of amino acid substitutions and dipeptide mimetics were studied. The most potent analogs exhibited a 50-to 100-fold improvement of in vitro activity over that of the phage-identified peptide sequence. (c) 2008 Elsevier Ltd. All rights reserved.