benzyl N-acetyl-4,6-O-benzylidene muramic acid | 115705-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl N-acetyl-4,6-O-benzylidene muramic acid
• 英文别名: benzyl (2R)-2-[[(4aR,7R,8R,8aS)-7-acetamido-6-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoate
• CAS: 115705-91-4
• 化学式: C₂₅H₂₉NO₈
• 分子量: 471.507
• InChiKey: VTKQKQPSOPYRMN-FZJVDLTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl (4R)-5-amino-4-[[(2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoyl]amino]-5-oxopentanoate 、 benzyl N-acetyl-4,6-O-benzylidene muramic acid 生成 benzyl (4R)-4-[[(2S)-2-[[(2R)-2-[[(4aR,7R,8R,8aS)-7-acetamido-6-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy]propanoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoyl]amino]-5-amino-5-oxopentanoate
  参考文献：
  名称：

  HIEBERT, C. K.;KOPP, W. C.;RICHERSON, H. B.;BARFKNECHT, C. F., J. MED. CHEM., 31,(1988) N 10, C. 2022-2024

  摘要：

  DOI：

文献信息

• Synthesis of fluorescent muramyl dipeptide congeners. 2
  作者：C. K. Hiebert、W. C. Kopp、H. B. Richerson、C. F. Barfknecht

  DOI：10.1021/jm00118a029

  日期：1988.10

  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.