N-acetylmuramoyl-L-alanyl-D-isoglutamine

• 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-acetylmuramoyl-L-alanyl-D-isoglutamine
• 英文别名: muramyl dipeptide；(4R)-4-[[(2S)-2-[[(2R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
• 化学式: C₁₉H₃₂N₄O₁₁
• 分子量: 492.483
• InChiKey: BSOQXXWZTUDTEL-PUFOHHGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  247
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  乙酸酐 、 (R)-5-amino-4-((S)-2-((R)-2-(((2R,3R,4R,5S)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-oxopentanoic acid 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 1.5h， 以37.931%的产率得到
  参考文献：
  名称：

  Peptidoglycan Modifications Tune the Stability and Function of the Innate Immune Receptor Nod2

  摘要：

  Natural modifications of peptidoglycan modulate the innate immune response. Peptidoglycan derivatives activate this response via the intracellular innate immune receptor, Nod2. To probe how these modifications alter the response, a novel and efficient carbohydrate synthesis was developed to allow for late-stage modification of the amine at the 2-position. Modification of the carbohydrate was found to be important for stabilizing Nod2 and generating the proper response. The native Nod2 ligands demonstrate a significant increase in the cellular stability of Nod2. Moreover, changing the identity of the natural ligands at the carbohydrate 2-position allows for the Nod2-dependent immune response to be either up-regulated or down-regulated. The ligand structure can be adjusted to tune the Nod2 response, suggesting that other innate immune receptors and their ligands could use a similar strategy.

  DOI：

  10.1021/jacs.5b01607

文献信息

• Peptidoglycan Modifications Tune the Stability and Function of the Innate Immune Receptor Nod2
  作者：James E. Melnyk、Vishnu Mohanan、Amy K. Schaefer、Ching-Wen Hou、Catherine Leimkuhler Grimes

  DOI：10.1021/jacs.5b01607

  日期：2015.6.10

  Natural modifications of peptidoglycan modulate the innate immune response. Peptidoglycan derivatives activate this response via the intracellular innate immune receptor, Nod2. To probe how these modifications alter the response, a novel and efficient carbohydrate synthesis was developed to allow for late-stage modification of the amine at the 2-position. Modification of the carbohydrate was found to be important for stabilizing Nod2 and generating the proper response. The native Nod2 ligands demonstrate a significant increase in the cellular stability of Nod2. Moreover, changing the identity of the natural ligands at the carbohydrate 2-position allows for the Nod2-dependent immune response to be either up-regulated or down-regulated. The ligand structure can be adjusted to tune the Nod2 response, suggesting that other innate immune receptors and their ligands could use a similar strategy.