dibenzylphospho-2,4-acetamido-3-O-benzoyl-2,4,6-deoxy-α-D-glucopyranoside | 868744-55-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dibenzylphospho-2,4-acetamido-3-O-benzoyl-2,4,6-deoxy-α-D-glucopyranoside
• CAS: 868744-55-2
• 化学式: C₃₁H₃₅N₂O₉P
• 分子量: 610.601
• InChiKey: WGNCQZKLZROFCD-CHSCONBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  138.49
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  dibenzylphospho-2,4-acetamido-3-O-benzoyl-2,4,6-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 168009.0h， 生成
  参考文献：
  名称：

  Investigating Bacterial N-Linked Glycosylation:  Synthesis and Glycosyl Acceptor Activity of the Undecaprenyl Pyrophosphate-Linked Bacillosamine

  摘要：

  The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can be used to investigate the activity of the enzyme PglA, which catalyzes the first glycosyl transfer in substrate biosynthesis for N-linked protein glycosylation in the pathogenic gram-negative bacterium. The availability of this synthetic substrate makes it possible to access polyprenyl-linked oligosaccharides, such as the GalNAc-alpha-1,3-bacillosamine-alpha-1-PP-Und intermediate, that will enable exploration of the remaining enzymes in the prokaryotic glycosylation pathway. Study of the bacterial glycosylation system will provide insight into the corresponding eukaryotic process, which is currently poorly understood.

  DOI：

  10.1021/ja054265v
• 作为产物：
  描述：

  benzyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-galactopyranoside 在 palladium dihydroxide 吡啶 、 palladium dihydroxide 、 sodium azide 、 氢气 、 sodium methylate 、 N,N-二异丙基乙胺 、 sodium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.17h， 生成 dibenzylphospho-2,4-acetamido-3-O-benzoyl-2,4,6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Investigating Bacterial N-Linked Glycosylation:  Synthesis and Glycosyl Acceptor Activity of the Undecaprenyl Pyrophosphate-Linked Bacillosamine

  摘要：

  The chemical synthesis and biological activity of undecaprenyl pyrophosphate bacillosamine (Und-PP-Bac), an obligatory intermediate in the asparagine-linked glycosylation pathway of Campylobacter jejuni, are reported. The key transformation involves the coupling of bacillosamine phosphate and undecaprenyl phosphate. The synthetic Und-PP-Bac can be used to investigate the activity of the enzyme PglA, which catalyzes the first glycosyl transfer in substrate biosynthesis for N-linked protein glycosylation in the pathogenic gram-negative bacterium. The availability of this synthetic substrate makes it possible to access polyprenyl-linked oligosaccharides, such as the GalNAc-alpha-1,3-bacillosamine-alpha-1-PP-Und intermediate, that will enable exploration of the remaining enzymes in the prokaryotic glycosylation pathway. Study of the bacterial glycosylation system will provide insight into the corresponding eukaryotic process, which is currently poorly understood.

  DOI：

  10.1021/ja054265v