(((4-azidobenzyl)oxy)carbonyl)-L-tryptophan | 1355358-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (((4-azidobenzyl)oxy)carbonyl)-L-tryptophan
• CAS: 1355358-67-6
• 化学式: C₁₉H₁₇N₅O₄
• 分子量: 379.375
• InChiKey: ZPEZRUABCKGKFU-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  140.18
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (((4-azidobenzyl)oxy)carbonyl)-L-tryptophan 、 (S)-(3-bromo-4,5-dihydroisoxazol-5-yl)methanamine 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 4-azidobenzyl ((S)-1-((((S)-3-bromo-4,5-dihydroisoxazol-5-yl)methyl)amino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  Dihydroisoxazole Analogs for Labeling and Visualization of Catalytically Active Transglutaminase 2

  摘要：

  We report the synthesis and preliminary characterization of "clickable" inhibitors of human transglutaminase 2 (TG2). These inhibitors possess the 3-halo-4,5-dihydroisoxazole warhead along with bioorthogonal groups such as azide or alkyne moieties that enable subsequent covalent modification with fluorophores. Their mechanism for inhibition of TG2 is based on halide displacement, resulting in the formation of a stable imino thioether. Inhibition assays against recombinant human TG2 revealed that some of the clickable inhibitors prepared in this study have comparable specificity as benchmark dihydroisoxazole inhibitors reported earlier. At low micromolar concentrations they completely inhibited transiently activated TG2 in a WI-38 fibroblast scratch assay and could subsequently be used to visualize the active enzyme in situ. The potential use of these inhibitors to probe the role of TG2 in celiac sprue as well as other diseases is discussed.

  DOI：

  10.1016/j.chembiol.2010.11.004