α-L-fucopyranosyl-(1->3)-β-L-fucopyranosyl azide | 1262032-73-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-fucopyranosyl-(1->3)-β-L-fucopyranosyl azide
• 英文别名: α-L-Fuc-(1->3)-β-L-Fuc-N3
• CAS: 1262032-73-4
• 化学式: C₁₂H₂₁N₃O₈
• 分子量: 335.314
• InChiKey: ITBDIUPRHMOUKC-NNUXCGHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.02
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177.6
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  β-L-Fucopyranosyl azide 在 sodium azide 、 Sulfolobus solfataricus α-L-fucosidase SsD242S mutant 作用下， 反应 16.0h， 生成 α-L-fucopyranosyl-(1->3)-β-L-fucopyranosyl azide
  参考文献：
  名称：

  β-Glycosyl Azides as Substrates for α-Glycosynthases: Preparation of Efficient α-L-Fucosynthases

  摘要：

  Fucose-containing oligosaccharides play a central role in physio-pathological events, and fucosylated oligosaccharides have interesting potential applications in biomedicine. No methods for the large-scale production of oligosaccharides are currently available, but the chemo-enzymatic approach is very promising. Glycosynthases, mutated glycosidases that synthesize oligosaccharides in high yields, have been demonstrated to be an interesting alternative. However, examples of glycosynthases available so far are restricted to a limited number of glycosidases families and to only one retaining alpha-glycosynthase. We show here that new mutants of two alpha-L-fucosidases are efficient alpha-L-fucosynthases. The approach shown utilized beta-L-fucopyranosyl azide as donor substrate leading to transglycosylation yields up to 91%. This is the first method exploiting a beta-glycosyl azide donor for alpha-glycosynthases; its applicability to the glycosynthetic methodology in a wider perspective is presented.

  DOI：

  10.1016/j.chembiol.2009.09.013