[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate | 515138-65-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: [(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate
• CAS: 515138-65-5
• 化学式: C₁₆H₂₅N₅O₁₅P₂
• 分子量: 589.347
• InChiKey: MHEUDODYXRJIEG-URARBOGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  265
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate 在 苯磺酰胺 、 copper(l) iodide 、 Tricine-NaOH buffer 、 vancomycin glucosyltransferase 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Diversifying Vancomycin via Chemoenzymatic Strategies

  摘要：

  [GRAPHICS]The rapid diversification of glycopeptides via glycorandomization reveals that significantly diverse substitutions are tolerated and suggests there may be a synergistic benefit to the construction of mechanistically related natural product core scaffold fusions. This work also further highlights the utility of chemoenzymatic approaches to diversify complex natural product architectures.

  DOI：

  10.1021/ol0501626
• 作为产物：
  描述：

  、 胸苷-5'-三磷酸 在 无机焦磷酸酶 、 nucleotidylyltransferase 、 Tris- HCl buffer 作用下， 反应 2.0h， 以95%的产率得到[(2R,3R,4S,5S,6R)-6-(azidomethyl)-3,4,5-trihydroxyoxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate
  参考文献：
  名称：

  Diversifying Vancomycin via Chemoenzymatic Strategies

  摘要：

  [GRAPHICS]The rapid diversification of glycopeptides via glycorandomization reveals that significantly diverse substitutions are tolerated and suggests there may be a synergistic benefit to the construction of mechanistically related natural product core scaffold fusions. This work also further highlights the utility of chemoenzymatic approaches to diversify complex natural product architectures.

  DOI：

  10.1021/ol0501626

文献信息

• Diversifying Vancomycin via Chemoenzymatic Strategies
  作者：Xun Fu、Christoph Albermann、Changsheng Zhang、Jon S. Thorson

  DOI：10.1021/ol0501626

  日期：2005.4.14

  [GRAPHICS]The rapid diversification of glycopeptides via glycorandomization reveals that significantly diverse substitutions are tolerated and suggests there may be a synergistic benefit to the construction of mechanistically related natural product core scaffold fusions. This work also further highlights the utility of chemoenzymatic approaches to diversify complex natural product architectures.