N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide | 22393-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
• CAS: 22393-17-5
• 化学式: C₂₀H₂₈N₂O₁₃
• 分子量: 504.448
• InChiKey: VWWSHNVLJCYYHC-GZDRNHDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.26
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  230.54
• 氢给体数：
  7.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  3-nitro-2-pyridyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 N-acetyl-β-hexosaminidase (Aspergillus oryzae) 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 N-{(2S,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide
  参考文献：
  名称：

  Nitropyridyl glycosides: new glycosyl donors for enzymatic transglycosylation

  摘要：

  New glycosyl donors, 3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides, proved to be effective for transglycosylation reaction catalyzed by glycosidases, such as beta-galactosidase, B-glucosidase, and N-acetyl-beta-hexosaminidase. The high solubility in water and the high reactivity of the nitropyridyl glycosides enabled the reactions under high concentrations of the donors and consequently rapid glycosyl transfer to glycosyl accepters. The yields of the transglycosylated products with the nitropyridyl glycosides were much higher than those with conventional p-nitrophenyl glycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01279-4