| 1354695-06-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1354695-06-9
• 化学式: C₂₆H₃₇N₅O₁₀S
• 分子量: 611.673
• InChiKey: ZNOIJDSXAGHTDJ-BHJGNOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  227.19
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  丹磺酰肼 、 N-acetylmuramoyl-L-alanine 在 三氯乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 生成 、
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Biotinyl Hydrazone Derivatives of Muramyl Peptides

  摘要：

  Muramyl peptides derived from bacterial peptidoglycan have long been known for their ability to trigger host innate immune responses, including inflammation and antimicrobial defense. Muramyl peptides have also been widely studied for their role as immune adjuvants. In mammals, the nucleotide‐binding oligomerization domain (Nod) proteins Nod1 and Nod2 detect distinct muramyl peptide structures and mediate their biological activity. Because of the poor immunogenicity of these small peptidoglycan derivatives, research in this field is currently limited by the lack of reagents to track or immobilize specific muramyl peptides. We present here the generation and initial biological characterization of synthetic muramyl peptides covalently coupled to dansyl or biotinyl derivatives and demonstrate that biotinyl coupling on the muramyl moiety results in derivatives that can be tracked by immunofluorescence and maintain full biological activity, as observed by their capacity to trigger Nod signaling. Moreover, using digitonin‐mediated permeabilization techniques on live cells, we also demonstrate that biotinylated muramyl peptides efficiently reach the host cytosol, where they activate Nod signaling. Therefore, these derivatives represent useful probes to study the cell biology and the biochemistry of host responses to muramyl peptides.

  DOI：

  10.1111/j.1747-0285.2011.01204.x