methyl 1-phospho-2,4-di-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate | 1062273-09-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-phospho-2,4-di-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate
• 英文别名: methyl (2R,3S,4S,5R,6R)-3,5-diacetyloxy-4-(2,2-dimethylpropanoyloxy)-6-phosphonooxyoxane-2-carboxylate
• CAS: 1062273-09-9
• 化学式: C₁₆H₂₅O₁₃P
• 分子量: 456.34
• InChiKey: XBBFYUIKMQGFPV-YCGPCKTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  181
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 1-phospho-2,4-di-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以14 mg的产率得到methyl 1-phospho-α-L-idopyranuronate monopyridinium salt
  参考文献：
  名称：

  Synthesis of Uridine 5′-diphosphoiduronic Acid: A Potential Substrate for the Chemoenzymatic Synthesis of Heparin

  摘要：

  An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5'-diphosphoiduronic acid (UDP-IdoA) and uridine 5'-diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5'-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

  DOI：

  10.1021/jo801409c
• 作为产物：
  描述：

  methyl 1-bromo-2,4-di-O-acetyl-3-O-pivaloyl-α-L-idopyranuronate 在 三乙胺 、 tetrabutylammonium phosphate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 methyl 1-phospho-2,4-di-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate
  参考文献：
  名称：

  Synthesis of Uridine 5′-diphosphoiduronic Acid: A Potential Substrate for the Chemoenzymatic Synthesis of Heparin

  摘要：

  An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5'-diphosphoiduronic acid (UDP-IdoA) and uridine 5'-diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5'-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

  DOI：

  10.1021/jo801409c