(11-azidoundecyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onic acid | 1338224-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (11-azidoundecyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onic acid
• 英文别名: (2R,4S,5R,6R)-5-acetamido-2-(11-azidoundecoxy)-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1338224-95-5
• 化学式: C₂₂H₄₀N₄O₉
• 分子量: 504.581
• InChiKey: UAFWVTZTOSZUGO-ZJGVECAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  35
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  180
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (11-azidoundecyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onic acid 、 胞苷-5'-单磷酸-N-乙酰神经氨酸 在 CST-II 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 以 水 为溶剂， 反应 24.0h， 以12%的产率得到11-azidoundecyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->8)-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid
  参考文献：
  名称：

  CST-II’s recognition domain for acceptor substrates in α-(2→8)-sialylations

  摘要：

  CST-II is a bacterial sialyltransferase known for its ability to perform alpha-(2 -> 8)-sialylations using GM(3) related trisaccharide substrates. Previously, we probed the enzyme's substrate specificity and developed an efficient synthesis for alpha-(2 -> 8)-oligosialosides, and we suggested that CST-II could have a very small substrate recognition domain. Here we report our full studies on CST-II's recognition feature for acceptor substrates. The current study further demonstrates the versatility of CST-II in preparing complex oligosaccharides that contain alpha-(2 -> 8)-oligosialyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.009
• 作为产物：
  描述：

  methyl (11-azidoundecyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 在 sodium methylate 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以64%的产率得到(11-azidoundecyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onic acid
  参考文献：
  名称：

  CST-II’s recognition domain for acceptor substrates in α-(2→8)-sialylations

  摘要：

  CST-II is a bacterial sialyltransferase known for its ability to perform alpha-(2 -> 8)-sialylations using GM(3) related trisaccharide substrates. Previously, we probed the enzyme's substrate specificity and developed an efficient synthesis for alpha-(2 -> 8)-oligosialosides, and we suggested that CST-II could have a very small substrate recognition domain. Here we report our full studies on CST-II's recognition feature for acceptor substrates. The current study further demonstrates the versatility of CST-II in preparing complex oligosaccharides that contain alpha-(2 -> 8)-oligosialyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.05.009

文献信息

• CST-II’s recognition domain for acceptor substrates in α-(2→8)-sialylations
  作者：Wenling Li、Ping Zhang、Amir J. Zuccolo、Ruxiang Blake Zheng、Chang-Chun Ling

  DOI：10.1016/j.carres.2011.05.009

  日期：2011.9

  CST-II is a bacterial sialyltransferase known for its ability to perform alpha-(2 -> 8)-sialylations using GM(3) related trisaccharide substrates. Previously, we probed the enzyme's substrate specificity and developed an efficient synthesis for alpha-(2 -> 8)-oligosialosides, and we suggested that CST-II could have a very small substrate recognition domain. Here we report our full studies on CST-II's recognition feature for acceptor substrates. The current study further demonstrates the versatility of CST-II in preparing complex oligosaccharides that contain alpha-(2 -> 8)-oligosialyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.