phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1-4)-3,6-di-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranoside | 27297-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1-4)-3,6-di-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranoside
• 英文别名: β-Phenyl-heptaacetyl-chitobiosid
• CAS: 27297-24-1
• 化学式: C₃₂H₄₂N₂O₁₆
• 分子量: 710.689
• InChiKey: ITVRJSOYLZJDJU-VPAFKTLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  50.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  226.62
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1-4)-3,6-di-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 β-Phenyl-di-N-acetyl-chitobiosid
  参考文献：
  名称：

  ‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

  摘要：

  N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-beta-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-alpha-1,3- and Man-alpha-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a beta-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

  DOI：

  10.1021/ja4056678
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 18.0h， 以380 mg的产率得到phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranosyl-(1-4)-3,6-di-O-acetyl-2-deoxy-2-N-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  ‘Naked’ and Hydrated Conformers of the Conserved Core Pentasaccharide of N-linked Glycoproteins and Its Building Blocks

  摘要：

  N-glycosylation of eukaryotic proteins is widespread and vital to survival. The pentasaccharide unit -Man(3)GlcNAc(2)- lies at the protein-junction core of all oligosaccharides attached to asparagine side chains during this process. Although its absolute conservation implies an indispensable role, associated perhaps with its structure, its unbiased conformation and the potential modulating role of solvation are unknown; both have now been explored through a combination of synthesis, laser spectroscopy, and computation. The proximal -GlcNAc-GlcNAc- unit acts as a rigid rod, while the central, and unusual, -Man-beta-1,4-GlcNAc- linkage is more flexible and is modulated by the distal Man-alpha-1,3- and Man-alpha-1,6- branching units. Solvation stiffens the 'rod' but leaves the distal residues flexible, through a beta-Man pivot, ensuring anchored projection from the protein shell while allowing flexible interaction of the distal portion of N-glycosylation with bulk water and biomolecular assemblies.

  DOI：

  10.1021/ja4056678