tributylammonium 5-deoxy-5-fluoro-α-D-galactofuranose monophosphate | 1391037-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tributylammonium 5-deoxy-5-fluoro-α-D-galactofuranose monophosphate
• CAS: 1391037-96-9
• 化学式: C₆H₁₂FO₈P*C₁₂H₂₇N
• 分子量: 447.482
• InChiKey: PXWBAMKMRVDMQT-GOCOMJOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  29.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  139.92
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl (3-methyl-1H-imidazol-3-ium-1-yl)phosphonate 、 tributylammonium 5-deoxy-5-fluoro-α-D-galactofuranose monophosphate 在 magnesium chloride 、 ammonium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.01h， 生成 5-deoxy-5-fluoro-α-D-galactofuranose uridine diphosphate
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzoyl-5-deoxy-5-fluoro-β-D-galactofuranoside 在 硫酸 、 palladium 10% on activated carbon 、 水 、 氢溴酸 、 氢气 、 碳酸氢铵 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 108.83h， 生成 tributylammonium 5-deoxy-5-fluoro-α-D-galactofuranose monophosphate
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p