5-acetamido-9-amino-2,6-anhydro-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid | 129178-62-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-acetamido-9-amino-2,6-anhydro-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid
• 英文别名: Neu5Ac9NH₂2en；9-Amino-2-deoxy-2,3-dehydro-n-acetyl-neuraminic acid；(2R,3R,4S)-3-acetamido-2-[(1R,2R)-3-amino-1,2-dihydroxypropyl]-4-hydroxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• CAS: 129178-62-7
• 化学式: C₁₁H₁₈N₂O₇
• 分子量: 290.273
• InChiKey: VJTPBNUXDULDQD-UFGQHTETSA-N

物化性质

• 沸点：
  746.5±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  162
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  戊酰氯 、 5-acetamido-9-amino-2,6-anhydro-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic acid 在 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以91%的产率得到5-acetamido-9-pentanamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid
  参考文献：
  名称：

  [EN] SIALIDASE INHIBITORS AND PREPARATION THEREOF
  [FR] INHIBITEURS DE SIALIDASE ET LEUR PRÉPARATION

  摘要：

  公开号：

  WO2018201058A3
• 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 26.0h， 生成 5-acetamido-9-amino-2,6-anhydro-3,5,9-trideoxy-D-glycero-D-galacto-non-2-enonic 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