methyl S-(5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->-6)-(6-thio-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside | 1338224-98-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: methyl S-(5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->-6)-(6-thio-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside
• 英文别名: (2S,4S,5R,6R)-5-acetamido-2-[[(2S,3R,4S,5R,6R)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methylsulfanyl]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1338224-98-8
• 化学式: C₂₄H₄₁NO₁₈S
• 分子量: 663.651
• InChiKey: ZHRBQWXHBPNYJO-HMPHPHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  340
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  methyl S-(5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->-6)-(6-thio-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside 、 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 72.0h， 以39%的产率得到methyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->8)-(5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->-6)-(6-thio-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  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：

  2-Thiosialic acid methyl ester peracetate 在 sodium methylate 、 二乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 methyl S-(5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->-6)-(6-thio-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranoside
  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.