3-azidopropyl β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→6)]-2-acetamido-2-deoxy-β-D-galactopyranoside | 1587693-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→6)]-2-acetamido-2-deoxy-β-D-galactopyranoside
• CAS: 1587693-17-1
• 化学式: C₂₈H₄₇N₅O₁₉
• 分子量: 757.703
• InChiKey: ALICLYKWVNXYRQ-OTGBOIBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.35
• 重原子数：
  52.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  381.71
• 氢给体数：
  12.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  N-acetyl neuraminic acid 、 3-azidopropyl β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→6)]-2-acetamido-2-deoxy-β-D-galactopyranoside 在 Neisseria CMP-sialic acid synthetase 、 Pasteurella multocida sialyltransferase M₁₄₄D mutant 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 以77%的产率得到3-azidopropyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→3)-β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→6)]-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Redox-Controlled Site-Specific α2–6-Sialylation

  摘要：

  The first bacterial alpha 2-6-sialyltransferase cloned from Photobacterium damselae (Pd2,6ST) has been widely applied for the synthesis of various alpha 2-6-linked sialosides. However, the extreme substrate flexibility of Pd2,6ST makes it unsuitable for site-specific alpha 2-6-sialylation of complex substrates containing multiple galactose and/or N-acetylgalactosamine units. To tackle this problem, a general redox-controlled site-specific sialylation strategy using Pd2,6ST is described. This approach features site-specific enzymatic oxidation of galactose units to mask the unwanted sialylation sites and precisely controlling the site-specific alpha 2-6-sialylation at intact galactose or N-acetylgalactosamine units.

  DOI：

  10.1021/jacs.9b00044
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 Neisseria CMP-sialic acid synthetase 、 Photobacterium damselae 2–6-sialyltransferase 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 1.0h， 生成 3-azidopropyl β-D-galactopyranosyl-(1→3)-[5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl-(2→6)]-2-acetamido-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Redox-Controlled Site-Specific α2–6-Sialylation

  摘要：

  The first bacterial alpha 2-6-sialyltransferase cloned from Photobacterium damselae (Pd2,6ST) has been widely applied for the synthesis of various alpha 2-6-linked sialosides. However, the extreme substrate flexibility of Pd2,6ST makes it unsuitable for site-specific alpha 2-6-sialylation of complex substrates containing multiple galactose and/or N-acetylgalactosamine units. To tackle this problem, a general redox-controlled site-specific sialylation strategy using Pd2,6ST is described. This approach features site-specific enzymatic oxidation of galactose units to mask the unwanted sialylation sites and precisely controlling the site-specific alpha 2-6-sialylation at intact galactose or N-acetylgalactosamine units.

  DOI：

  10.1021/jacs.9b00044

文献信息

• Regioselective Chemoenzymatic Synthesis of Ganglioside Disialyl Tetrasaccharide Epitopes
  作者：Xin Meng、Wenlong Yao、Jiansong Cheng、Xu Zhang、Lan Jin、Hai Yu、Xi Chen、Fengshan Wang、Hongzhi Cao

  DOI：10.1021/ja5000609

  日期：2014.4.9

  A novel chemoenzymatic approach for the synthesis of disialyl tetrasaccharide epitopes found as the terminal oligosaccharides of GD1 alpha, GT1a alpha, and GQ1b alpha is described. It relies on chemical manipulation of enzymatically generated trisaccharides as conformationally constrained acceptors for regioselective enzymatic alpha 2-6-sialylation. This strategy provides a new route for easy access to disialyl tetrasaccharide epitopes and their derivatives.