β-methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside | 1446514-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R)-2-[(2R,3S,4R,5R,6R)-5-acetamido-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(1R)-1-carboxyethoxy]-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxypropanoic acid
• CAS: 1446514-29-9
• 化学式: C₃₉H₆₄N₄O₂₅
• 分子量: 988.949
• InChiKey: OMQNONODQNQQTO-SIQXZOKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.52
• 重原子数：
  68.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  424.91
• 氢给体数：
  13.0
• 氢受体数：
  23.0

反应信息

• 作为产物：
  描述：

  在 溶剂黄146 、 palladium 10% on activated carbon 作用下， 以 甲醇 为溶剂， 反应 19.0h， 以46%的产率得到β-methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-3-O-((R)-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Reaction Products and the X-ray Structure of AmpDh2, a Virulence Determinant of Pseudomonas aeruginosa

  摘要：

  The zinc protease AmpDh2 is a virulence determinant of Pseudomonas aeruginosa, a problematic human pathogen. The mechanism of how the protease manifests virulence is not known, but it is known that it turns over the bacterial cell wall. The reaction of AmpDh2 with the cell wall was investigated, and nine distinct turnover products were characterized by LC/MS/MS. The enzyme turns over both the cross-linked and noncross-linked cell wall. Three high-resolution X-ray structures, the apo enzyme and two complexes with turnover products, were solved. The X-ray structures show how the dimeric protein interacts with the inner leaflet of the bacterial outer membrane and that the two monomers provide a more expansive surface for recognition of the cell wall. This binding surface can accommodate the 3D solution structure of the cross-linked cell wall.

  DOI：

  10.1021/ja405464b