N-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl-N-DTAF-L-lysine | 115705-90-3

• 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: N-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl-N-DTAF-L-lysine
• CAS: 115705-90-3
• 化学式: C₄₈H₅₄ClN₁₀O₁₇*K
• 分子量: 1117.56
• InChiKey: ONFLYVRBADEPBM-WAMUCTKUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.02
• 重原子数：
  77.0
• 可旋转键数：
  24.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  429.24
• 氢给体数：
  12.0
• 氢受体数：
  21.0

反应信息

• 作为产物：
  描述：

  2-(fluoresceinylamino)-4,6-dichloro-s-triazine 、 (2S)-2-{[(2R)-2-({(2S)-2-[(2-{[(2S,3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}propanoyl)amino]propanoyl}amino)-5-amino-5-oxopentanoyl]amino}-6-aminohexanoic a cid 在 potassium carbonate 作用下， 以 水 为溶剂， 以61%的产率得到N-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl-N-DTAF-L-lysine
  参考文献：
  名称：

  Synthesis of fluorescent muramyl dipeptide congeners. 2

  摘要：

  Muramyl dipeptide (MDP) analogues were prepared and utilized in the synthesis of new fluorescently labeled MDP derivatives for use as biologic probes. Thus, N alpha-(N-acetylmuramyl)-L-lysyl-D-isoglutamine (Lys-MDP, 4) and N alpha-(N-acetylmuramyl)-L-alanyl-D-isoglutaminyl)-L-lysine [MTP, 5] were synthesized and then reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to yield the fluorescent adducts, DTAF-Lys-MDP (6) and DTAF-MTP (7). The adjuvant activity of the fluorescent MDP derivatives was determined by the ability of the compounds to promote delayed skin test responses in guinea pigs immunized with ovalbumin (OA) and by evaluating the anti-OA activity of these guinea pigs.

  DOI：

  10.1021/jm00118a029