(S)-aziridine-2-carboxaldehyde | 1000072-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丙烷
• 英文名称: (S)-aziridine-2-carboxaldehyde
• 英文别名: (2S)-aziridine-2-carbaldehyde
• CAS: 1000072-66-1
• 化学式: C₃H₅NO
• 分子量: 71.0788
• InChiKey: XINHDFIDPBPOHI-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  39
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-aziridine-2-carboxaldehyde 、 苯丙氨酸苯胺 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 Az-Phe-An
  参考文献：
  名称：

  Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates

  摘要：

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.

  DOI：

  10.1021/ja104488d