N-acetyl-6-thioneuraminic acid | 109201-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: N-acetyl-6-thioneuraminic acid
• 英文别名: 6-thio-NeuAc；(2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2-carboxylic acid
• CAS: 109201-76-5
• 化学式: C₁₁H₁₉NO₈S
• 分子量: 325.34
• InChiKey: NVJIKGKSTHUSMD-PFQGKNLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  193
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-acetyl-6-thioneuraminic acid 以 吡啶 为溶剂， 生成 5-Acetamido-2,6-anhydro-3,5-didesoxy-6-thio-D-glycero-D-galacto-non-2-ensaeure
  参考文献：
  名称：

  Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid

  摘要：

  DOI：

  10.1016/s0040-4039(00)95683-1
• 作为产物：
  描述：

  (2S,3R,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]thiane-2,3-dicarboxylic acid 在 溶剂黄146 作用下， 反应 5.0h， 以175 mg的产率得到N-acetyl-6-thioneuraminic acid
  参考文献：
  名称：

  Synthese von 6-thiosialinsäuren

  摘要：

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00167-7

文献信息

• Method of producing 6-thio-sialylated glycoproteins and glycoconjugates
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：EP1911850A1

  公开（公告）日：2008-04-16

  The present invention relates to a method of preparing 6-thio-sialyl-glycosyl compounds, comprising the step consisting of reacting in vitro or in vivo 6-thio-sialic acid compounds with a CMP-sialic synthetase to form CMP-6-thio sialic acid compounds and with a sialyltransferase to transfer said CMP-6-thio sialic acid compounds as donor substrate to glycosyl compounds as acceptor subtrate leading to the enzymatic coupling of 6-thiosialic acid compounds onto glycosyl compounds. Glycosyl compounds are selected from glycoproteins, glycolipids and oligosaccharides, including monoclonal antibodies.

  本发明涉及一种制备6-硫代硅烷基-糖基化合物的方法，包括以下步骤：在体外或体内将6-硫代硅烷基化合物与CMP-硅烷基合成酶反应，形成CMP-6-硫代硅烷基化合物，并与硅烷基转移酶反应，将所述CMP-6-硫代硅烷基化合物作为供体底物转移到作为受体底物的糖基化合物上，导致6-硫代硅烷基化合物与糖基化合物的酶偶联。糖基化合物可选自糖蛋白、糖脂和寡糖，包括单克隆抗体。
• Synthesis of 6-thiosialic acids and 6-thio-N-acetyl-D-neuraminic acid
  作者：H Mack、R Brossmer

  DOI：10.1016/s0040-4039(00)95683-1

  日期：——
• Synthese von 6-thiosialinsäuren
  作者：Hans Mack、Reinhard Brossmer

  DOI：10.1016/s0040-4020(98)00167-7

  日期：1998.4

  The synthesis of 2-acetamido-2-deoxy-3-thio-D-mannose (11) is described. Chain elongation of thiazoline 10 with potassium-di-O-tbutyl-oxaloacetate yields epimeric 6-thiosialic acids 14 and 15. Chain extension of 18 with oxaloacetate/Ni++ results in the formation of N-acetyl-6-thioneuraminic acid (21). Starting from 21 synthesis of alpha-azide 25 and dehydro-compound 27 was accomplished by treatment of 23 with sodium azide. On the other hand lewis acid catalyzed azidation of 22 beta with azidotrimethylsilane afforded beta-azide 29. (C) 1998 Elsevier Science Ltd. All rights reserved.