GM1-五糖 | 52659-37-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: GM1-五糖
• 英文名称: LS-tetrasaccharide a
• 英文别名: sialyllacto-N-tetraose a；α-D-Neu5Ac-(2→3)-β-D-Gal-(1→3)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-β-D-Glc；GM1-Pentasaccharide；(2S,4S,5R,6R)-5-acetamido-2-[(2R,3R,4S,5S,6R)-2-[(2S,3R,4R,5S,6R)-3-acetamido-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 52659-37-7
• 化学式: C₃₇H₆₂N₂O₂₉
• 分子量: 998.895
• InChiKey: IOAPDMZSLCJVCR-XWSXOIAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.4
• 重原子数：
  68
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  502
• 氢给体数：
  19
• 氢受体数：
  29

反应信息

• 作为反应物：
  描述：

  GM1-五糖 在 碳酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以79%的产率得到(2S,4S,5R,6R)-5-acetamido-2-(((2R,3R,4S,5S,6R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(((2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-6-amino-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Bioorthogonal human milk oligosaccharide probes for antimicrobial target identification within Streptococcus agalactiae

  摘要：

  Human milk oligosaccharides (HMOs) are a structurally diverse class of carbohydrates that possess strong antibacterial activity against Streptococcus agalactiae (Group B Strep, GBS). This work highlights the design, synthesis, and retained biological activity of several HMO bioorthogonal probes within GBS, a first in class advance. The use of such probes will assist in identifying HMO-protein interactions within GBS and may be broadly applicable in researching HMO cellular targets within a variety of biological systems. Finally, this strategy is highly amenable to other oligosaccharide scaffolds, requiring minimal synthetic transformations and chemical perturbation.

  DOI：

  10.1016/j.carres.2019.107895

文献信息

• Bioorthogonal human milk oligosaccharide probes for antimicrobial target identification within Streptococcus agalactiae
  作者：Schuyler A. Chambers、Steven D. Townsend

  DOI：10.1016/j.carres.2019.107895

  日期：2020.2

  Human milk oligosaccharides (HMOs) are a structurally diverse class of carbohydrates that possess strong antibacterial activity against Streptococcus agalactiae (Group B Strep, GBS). This work highlights the design, synthesis, and retained biological activity of several HMO bioorthogonal probes within GBS, a first in class advance. The use of such probes will assist in identifying HMO-protein interactions within GBS and may be broadly applicable in researching HMO cellular targets within a variety of biological systems. Finally, this strategy is highly amenable to other oligosaccharide scaffolds, requiring minimal synthetic transformations and chemical perturbation.