benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside | 40656-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside
• CAS: 40656-45-9
• 化学式: C₁₅H₂₀BrNO₅
• 分子量: 374.232
• InChiKey: TWGNGBDUBZIUPY-RYPNDVFKSA-N

物化性质

• 沸点：
  592.5±50.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  88.02
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside 在 sodium sulfite 作用下， 以 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of an N-acetylglucosamine biosynthesis inhibitor

  摘要：

  The structural rationale, synthesis and evaluation of an inhibitor designed to block glucosamine synthesis by competitively inhibiting the action of glutamine: fructose-6-phosphate amidotransferase and subsequently reducing the transformation of any glucosamine-6-phosphate formed to UDP-N-acetylglucosamine are described. The inhibitor 2-acetamido-2,6-dideoxy-6-sulfo-D-glucose (D-glucosamine-6-sulfonate) is an analog of glucosamine-6-phosphate in which the phosphate group in the latter is replaced with a sulfonic acid group. The inhibitor is designed to function by three different modes which together reduce UDP-N-acetylglucosamine synthesis. This reduction was confirmed by evaluating the effect of the inhibitor on bacterial cell-wall synthesis and by demonstrating that it inhibits acetylation of glucosamine-6-phosphate competitively and by acting as a surrogate substrate. Inhibition of glucosamine production or suitably activated glucosamine in bacteria leads to disruption of the peptidoglycan structure, which results in softening, bulging, deformation, fragility and lysis of the cells. These modifications were documented by scanning electron microscopy for bacteria treated with the inhibitor. They were observed for inhibitor concentrations in the 20 mg/mL range for Escherichia coli and Bacillus subtilis and the 5 mg/mL range for Rhizobium (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.004
• 作为产物：
  描述：

  benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 在 吡啶 、 四溴化碳 、 三苯基膦 作用下， 反应 0.75h， 以44%的产率得到benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Preparative routes to methyl 2-acetamido-2,6-dideoxy-α-d-glucopyranoside

  摘要：

  DOI：

  10.1016/0008-6215(83)84058-0