| 865262-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 865262-81-3
• 化学式: C₃₃H₅₅N₅O₂₄
• 分子量: 905.819
• InChiKey: FIDFNIHLZUBUKT-IMEVZVBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.92
• 重原子数：
  62.0
• 可旋转键数：
  19.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  460.86
• 氢给体数：
  15.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  在 GalNAcE 、 ST₃Gal-I 、 manganese(ll) chloride 作用下， 以 alkaline aq. solution 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a

  摘要：

  We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, alpha-(2 -> 3/8)-sialyltransferase (Cst-II), beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CgtA), and beta-(1 -> 3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 4) -beta-(D)-Glcp-), GT3 (alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GM2 (beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GD2 (beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GT2 (beta-(D)-GalpNAc-(1 -> 4)-[(alpha-(D)-Neup5Ac-(2 -> 8)]-beta-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> -> 3)beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), and GM1 (beta-(D)-Galp-(1 -> 3)-beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp(1 -> 4)-beta-(D)-Glcp-) were synthesized in high yields (gram-scale). In addition, a mammalian a-(2 3)-sialyltransferase (ST3Gal 1) was used to sialylate GM1 and generate GD1a (alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 3)-beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-) oligosaccharide. We also cloned and expressed a rat UDP-N-acetylglucosamine-4 '-epimerase (GaINAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GIcNAc to UDP-GaINAc. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.008
• 作为产物：
  描述：

  uridine-5'-diphospho-N-acetyl-D-galactosamine 、 (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-(2-azidoethoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid 在 GalNAcE nicotinamide adenine dinucleotide 、 manganese(ll) chloride 作用下， 以 alkaline aq. solution 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Chemoenzymatic synthesis of 2-azidoethyl-ganglio-oligosaccharides GD3, GT3, GM2, GD2, GT2, GM1, and GD1a

  摘要：

  We have synthesized several ganglio-oligosaccharide structures using glycosyltransferases from Campylobacter jejuni. The enzymes, alpha-(2 -> 3/8)-sialyltransferase (Cst-II), beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CgtA), and beta-(1 -> 3)-galactosyltransferase (CgtB), were produced in large-scale fermentation from Escherichia coli and further characterized based on their acceptor specificities. 2-Azidoethyl-glycosides corresponding to the oligosaccharides of GD3 (alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 4) -beta-(D)-Glcp-), GT3 (alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GM2 (beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GD2 (beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), GT2 (beta-(D)-GalpNAc-(1 -> 4)-[(alpha-(D)-Neup5Ac-(2 -> 8)]-beta-(D)-Neup5Ac-(2 -> 8)-alpha-(D)-Neup5Ac-(2 -> -> 3)beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-), and GM1 (beta-(D)-Galp-(1 -> 3)-beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp(1 -> 4)-beta-(D)-Glcp-) were synthesized in high yields (gram-scale). In addition, a mammalian a-(2 3)-sialyltransferase (ST3Gal 1) was used to sialylate GM1 and generate GD1a (alpha-(D)-Neup5Ac-(2 -> 3)-beta-(D)-Galp-(1 -> 3)-beta-(D)-GalpNAc-(1 -> 4)-[alpha-(D)-Neup5Ac-(2 -> 3)]-beta-(D)-Galp-(1 -> 4)-beta-(D)-Glcp-) oligosaccharide. We also cloned and expressed a rat UDP-N-acetylglucosamine-4 '-epimerase (GaINAcE) in E. coli AD202 cells for cost saving in situ conversion of less expensive UDP-GIcNAc to UDP-GaINAc. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.06.008