4-nitrophenyl 6-phospho-β-D-glucoside | 55196-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 6-phospho-β-D-glucoside
• 英文别名: 4NPβG6P；((2R,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-nitrophenoxy)tetrahydro-2H-pyran-2-yl)methyl dihydrogen phosphate；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-nitrophenoxy)oxan-2-yl]methyl dihydrogen phosphate
• CAS: 55196-70-8
• 化学式: C₁₂H₁₆NO₁₁P
• 分子量: 381.233
• InChiKey: ULWWOIRVCLMNOB-RMPHRYRLSA-N

物化性质

• 沸点：
  704.5±70.0 °C(Predicted)
• 密度：
  1.761±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  192
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-硝基苯-Β-D-吡喃葡萄糖苷 在 β-glucosidase kinase from Klebsiella pneumonia 、 magnesium sulfate 、 5’-三磷酸腺苷 作用下， 以 aq. buffer 为溶剂， 反应 2.0h， 生成 4-nitrophenyl 6-phospho-β-D-glucoside
  参考文献：
  名称：

  Cross-utilization of β-galactosides and cellobiose in Geobacillus stearothermophilus

  摘要：

  Strains of the Gram-positive, thermophilic bacteriumGeobacillus stearothermophiluspossess elaborate systems for the utilization of hemicellulolytic polysaccharides, including xylan, arabinan, and galactan. These systems have been studied extensively in strains T-1 and T-6, representing microbial models for the utilization of soil polysaccharides, and many of their components have been characterized both biochemically and structurally. Here, we characterized routes by whichG. stearothermophilusutilizes mono- and disaccharides such as galactose, cellobiose, lactose, and galactosyl-glycerol. TheG. stearothermophilusgenome encodes a phosphoenolpyruvate carbohydrate phosphotransferase system (PTS) for cellobiose. We found that the cellobiose-PTS system is induced by cellobiose and characterized the corresponding GH1 6-phospho-beta-glucosidase, Cel1A. The bacterium also possesses two transport systems for galactose, a galactose-PTS system and an ABC galactose transporter. The ABC galactose transport system is regulated by a three-component sensing system. We observed that both systems, the sensor and the transporter, utilize galactose-binding proteins that also bind glucose with the same affinity. We hypothesize that this allows the cell to control the flux of galactose into the cell in the presence of glucose. Unexpectedly, we discovered thatG. stearothermophilusT-1 can also utilize lactose and galactosyl-glycerol via the cellobiose-PTS system together with a bifunctional 6-phospho-beta-gal/glucosidase, Gan1D. Growth curves of strain T-1 growing in the presence of cellobiose, with either lactose or galactosyl-glycerol, revealed initially logarithmic growth on cellobiose and then linear growth supported by the additional sugars. We conclude that Gan1D allows the cell to utilize residual galactose-containing disaccharides, taking advantage of the promiscuity of the cellobiose-PTS system.

  DOI：

  10.1074/jbc.ra120.014029