(2R,3R,4R,5S)-3-(((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((4-nitrobenzyl)amino)hexane-1,2,4,5-tetraol | 1363444-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5S)-3-(((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((4-nitrobenzyl)amino)hexane-1,2,4,5-tetraol
• 英文别名: 1-p-nitrobenzyl-(2-fucosyl)-lactose
• CAS: 1363444-62-5
• 化学式: C₂₅H₄₀N₂O₁₆
• 分子量: 624.596
• InChiKey: JOFMNRGMJIFDPH-MRCSSLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  43.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  294.39
• 氢给体数：
  11.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-3-(((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((4-nitrobenzyl)amino)hexane-1,2,4,5-tetraol 、 uridine 5'-diphospho-2-azidoacetamido-2-deoxy-α-D-galactopyranose 在 recombinant human blood group A antigen glycosyltransferase 作用下， 生成
  参考文献：
  名称：

  Chemoenzymatic Probes for Detecting and Imaging Fucose-α(1-2)-galactose Glycan Biomarkers

  摘要：

  The disaccharide motif fucose-alpha(1-2)-galactose (Fuc alpha(1-2)Gal) is involved in many important physiological processes, such as learning and memory, inflammation, asthma, and tumorigenesis. However, the size and structural complexity of Fuc alpha(1-2) Gal-containing glycans have posed a significant challenge to their detection. We report a new chemoenzymatic strategy for the rapid, sensitive detection of Fuc alpha(1-2)Gal glycans. We demonstrate that the approach is highly selective for the Fuc alpha(1-2)Gal motif, detects a variety of complex glycans and glycoproteins, and can be used to profile the relative abundance of the motif on live cells, discriminating malignant from normal cells. This approach represents a new potential strategy for biomarker detection and expands the technologies available for understanding the roles of this important class of carbohydrates in physiology and disease.

  DOI：

  10.1021/ja211312u
• 作为产物：
  描述：

  4-硝基苄胺 、 2'-O-fucosyllactose 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以56%的产率得到(2R,3R,4R,5S)-3-(((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-((4-nitrobenzyl)amino)hexane-1,2,4,5-tetraol
  参考文献：
  名称：

  Method of detecting cancer based on glycan biomarkers

  摘要：

  本发明提供了一种用特定糖基标记或检测蛋白质的方法。这些方法特别适用于检测包含检测到的糖基的癌细胞。本发明还提供了标记剂和检测剂、标记的蛋白质和混合物，以及相关的试剂盒和阵列。

  公开号：

  US09766245B2