| 860783-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 860783-64-8
• 化学式: C₃₆H₆₁N₃O₂₇
• 分子量: 967.884
• InChiKey: MZXHMQUJHDZYIT-NSUZPCKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.07
• 重原子数：
  66.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  495.65
• 氢给体数：
  18.0
• 氢受体数：
  26.0

反应信息

• 作为反应物：
  描述：

  、 氯甲酸-9-芴基甲酯 在 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 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：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 10% palladium on active carbon Cst-II enzyme 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 manganese(ll) chloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 61.0h， 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

文献信息

• Enhanced Sialylating Activity of O-Chloroacetylated 2-Thioethyl Sialosides
  作者：Yury E. Tsvetkov、Nikolay E. Nifantiev

  DOI：10.1055/s-2005-868514

  日期：——

  It has been shown that O-chloroacetyl protecting groups enhance significantly sialylating activity of 2-thioethyl sialosides in model reactions of α(2-8)-sialylation. Ethyl 4,7,8,9-tetra-O-chloroacetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-d-glycero-α-d-galacto-non-2-ulopyranoside that combines electron-withdrawing O-chloroacetyl and N-trifluoroacetyl protecting groups displayed the best reactivity and enabled the most efficient synthesis of the Neu5Acα(2-8)Neu5Ac dimer. The GD3 tetrasaccharide was synthesized in stepwise manner using this sialyl donor in the key (2-8)-coupling, albeit the yield was noticeably lower than in the model sialylation of monosaccharide acceptors.

  研究表明，O-氯乙酰保护基团显著提高了2-巯乙基唾液酸苷在α(2-8)-唾液酸化模型反应中的活性。乙基4,7,8,9-四-O-氯乙酰-3,5-二脱氧-2-硫-5-三氟乙酰胺基-d-甘油-α-d-半乳糖-壬-2-烯呋喃糖苷结合了吸电子的O-氯乙酰和N-三氟乙酰保护基团，展现出最佳的反应活性，并实现了Neu5Acα(2-8)Neu5Ac二聚体的最高效合成。通过使用这种唾液酸供体，以分步方式合成了GD3四糖，尽管其产率明显低于单糖受体的模型唾液酸化反应。