5-acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid | 208591-61-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid
• 英文别名: 5-acetamido-2,6-anhydro-9-(4-carboxybutanamido)-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid；(2R,3R,4S)-3-acetamido-2-[(1R,2R)-3-(4-carboxybutanoylamino)-1,2-dihydroxypropyl]-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 208591-61-1
• 化学式: C₁₆H₂₄N₂O₁₀
• 分子量: 404.374
• InChiKey: DLDXETGOWJUNDZ-NIQAVCIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  203
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 在 吡啶 、 sodium hydroxide 、 sodium azide 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.33h， 生成 5-acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Synthesis of a Neu2en5Ac analog hapten and isolation of monoclonal antibody to Neu2en5Ac

  摘要：

  Neu2en5Ac is a minor component of body fluids and is abundant in sialuria, but no antibody to detect it has been reported. 5-Acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid has been synthesized and conjugated with keyhole limpet hemocyanin (KLH) for immunization. A hybridoma named SIC172 was obtained that produces a monoclonal antibody (MAb) to Neu2en5Ac. SIC172 MAb in culture supernatant bound strongly to the hapten conjugated to BSA in ELISA, but slightly to fetuin, a glycoprotein which is rich in Neu5Ac. SIC172 MAb (IgG3(kappa)), purified with a protein A/G affinity column, bound strongly to fetuin. Neu2en5Ac competed with the MAb in binding in amounts as low as 3 mu M, while the competition of Neu5Ac appeared at amounts of more than 300 mu M. SIC172 MAb is a unique MAb specific to Neu2en5Ac and might be useful for detecting Neu2en5Ac, which occurs naturally and in sialuria. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00023-3

文献信息

• Synthesis of a Neu2en5Ac analog hapten and isolation of monoclonal antibody to Neu2en5Ac
  作者：Hiroya Kamei、Yasuhiro Kajihara、Yoshisuke Nishi

  DOI：10.1016/s0008-6215(99)00023-3

  日期：1999.2

  Neu2en5Ac is a minor component of body fluids and is abundant in sialuria, but no antibody to detect it has been reported. 5-Acetamido-2,6-anhydro-9-glutaramido-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid has been synthesized and conjugated with keyhole limpet hemocyanin (KLH) for immunization. A hybridoma named SIC172 was obtained that produces a monoclonal antibody (MAb) to Neu2en5Ac. SIC172 MAb in culture supernatant bound strongly to the hapten conjugated to BSA in ELISA, but slightly to fetuin, a glycoprotein which is rich in Neu5Ac. SIC172 MAb (IgG3(kappa)), purified with a protein A/G affinity column, bound strongly to fetuin. Neu2en5Ac competed with the MAb in binding in amounts as low as 3 mu M, while the competition of Neu5Ac appeared at amounts of more than 300 mu M. SIC172 MAb is a unique MAb specific to Neu2en5Ac and might be useful for detecting Neu2en5Ac, which occurs naturally and in sialuria. (C) 1999 Elsevier Science Ltd. All rights reserved.