α-(2->8)-trisialic acid | 180521-51-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(2->8)-trisialic acid
• 英文别名: alpha-Neup5Ac-(2->8)-alpha-Neup5Ac-(2->8)-beta-Neup5Ac；(2S,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-carboxy-4-hydroxyoxan-2-yl]oxy-1,3-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
• CAS: 180521-51-1
• 化学式: C₃₃H₅₃N₃O₂₅
• 分子量: 891.789
• InChiKey: ZFOIZUZRBOTSMP-GHUXNPPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.4
• 重原子数：
  61
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  468
• 氢给体数：
  17
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  α-(2->8)-trisialic acid 在 溶剂黄146 作用下， 反应 8.0h， 生成 (2S,4S,5R,6R)-5-acetamido-6-[(S)-[(2R,6S,8R,9R,10S)-9-acetamido-8-[(S)-[(2R,6S,8R,9R,10S)-9-acetamido-10-hydroxy-5-oxo-8-[(1R,2R)-1,2,3-trihydroxypropyl]-1,4,7-trioxaspiro[5.5]undecan-2-yl]-hydroxymethyl]-10-hydroxy-5-oxo-1,4,7-trioxaspiro[5.5]undecan-2-yl]-hydroxymethyl]-2,4-dihydroxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Regioselective Lactonization ofα-(2→8)-Trisialic Acid

  摘要：

  A simple and selective method has been developed to obtain both monolactones of the title compound, a model compound for biologically important polyneuraminic acid derivatives: acidic lactonization and alkaline hydrolysis of dilactone 1. The two monolactonized trimers can be separated by capillary electrophoresis, and then distinguished by enzymatic hydrolysis with neuraminidase; only the 2-monolactone undergoes reaction.

  DOI：

  10.1002/(sici)1521-3773(19990301)38:5<686::aid-anie686>3.0.co;2-p

文献信息

• Regioselective Lactonization ofα-(2→8)-Trisialic Acid
  作者：Mou-Chi Cheng、Chun-Hung Lin、Kay-Hooi Khoo、Shih-Hsiung Wu

  DOI：10.1002/(sici)1521-3773(19990301)38:5<686::aid-anie686>3.0.co;2-p

  日期：1999.3.1

  A simple and selective method has been developed to obtain both monolactones of the title compound, a model compound for biologically important polyneuraminic acid derivatives: acidic lactonization and alkaline hydrolysis of dilactone 1. The two monolactonized trimers can be separated by capillary electrophoresis, and then distinguished by enzymatic hydrolysis with neuraminidase; only the 2-monolactone undergoes reaction.