(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxyoxane-2-carboxylic acid | 71536-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxyoxane-2-carboxylic acid
• CAS: 71536-86-2
• 化学式: C₁₂H₂₀O₁₁
• 分子量: 340.284
• InChiKey: JRRMYAOAFIXYNJ-UUGJNZGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  UDP-GlcNTFA 、 (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R)-4-hydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxyoxane-2-carboxylic acid 在 Escherichia coli K₅ N-acetyl-D-glucosaminyl transferase 、 magnesium chloride 作用下， 生成
  参考文献：
  名称：

  Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*

  摘要：

  Heparan sulfate is a sulfated glycan that exhibits essential physiological functions. Interrogation of the specificity of heparan sulfate-mediated activities demands a library of structurally defined oligosaccharides. Chemical synthesis of large heparan sulfate oligosaccharides remains challenging. We report the synthesis of oligosaccharides with different sulfation patterns and sizes from a disaccharide building block using glycosyl-transferases, heparan sulfate C-5-epimerase, and sulfotransferases. This method offers a generic approach to prepare heparan sulfate oligosaccharides possessing predictable structures.

  DOI：

  10.1074/jbc.m110.159152

文献信息

• Chemoenzymatic Design of Heparan Sulfate Oligosaccharides*
  作者：Renpeng Liu、Yongmei Xu、Miao Chen、Michel Weïwer、Xianxuan Zhou、Arlene S. Bridges、Paul L. DeAngelis、Qisheng Zhang、Robert J. Linhardt、Jian Liu

  DOI：10.1074/jbc.m110.159152

  日期：2010.10

  Heparan sulfate is a sulfated glycan that exhibits essential physiological functions. Interrogation of the specificity of heparan sulfate-mediated activities demands a library of structurally defined oligosaccharides. Chemical synthesis of large heparan sulfate oligosaccharides remains challenging. We report the synthesis of oligosaccharides with different sulfation patterns and sizes from a disaccharide building block using glycosyl-transferases, heparan sulfate C-5-epimerase, and sulfotransferases. This method offers a generic approach to prepare heparan sulfate oligosaccharides possessing predictable structures.