dodecyl 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-ulopyranosidonic acid | 1186201-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dodecyl 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-ulopyranosidonic acid
• 英文别名: NeuAc(a2-8)NeuAc(a)-Sdodecyl；(2S,4S,5R,6R)-5-acetamido-2-[(1S,2R)-1-[(2R,3R,4S,6S)-3-acetamido-6-carboxy-6-dodecylsulfanyl-4-hydroxyoxan-2-yl]-1,3-dihydroxypropan-2-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 1186201-35-3
• 化学式: C₃₄H₆₀N₂O₁₆S
• 分子量: 784.92
• InChiKey: KQYOZIFHTWQUPU-NZGVHPCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  327
• 氢给体数：
  11
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  1-碘十二烷 在 甲醇 、 CST-II (α-2,8-sialyltransferase) from Campylobacter jejuni OH4384 、 potassium tert-butylate 、 二乙胺 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 66.75h， 生成 dodecyl 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-ulopyranosidonic acid 、 dodecyl 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-ulopyranosylonic acid)-(2->8)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid
  参考文献：
  名称：

  Probing a sialyltransferase’s recognition domain to prepare α(2,8)-linked oligosialosides and analogs

  摘要：

  我们首次观察到，单唾液酸残基是酶CST-II识别的关键结构要素；这一发现为一步合成一系列α(2,8)-连接的寡唾液酸及其硫代类似物开辟了一条有吸引力的途径。

  DOI：

  10.1039/b908933k

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.
• Probing a sialyltransferase’s recognition domain to prepare α(2,8)-linked oligosialosides and analogs
  作者：Ping Zhang、Amir J. Zuccolo、Wenling Li、Ruixiang Blake Zheng、Chang-Chun Ling

  DOI：10.1039/b908933k

  日期：——

  We report the first observation that a monosialyl residue is the essential structural element recognized by the enzyme CST-II; this has resulted in an attractive route to synthesize a series of α(2,8)-linked oligosialic acids and their thioanalogs in one step.

  我们首次观察到，单唾液酸残基是酶CST-II识别的关键结构要素；这一发现为一步合成一系列α(2,8)-连接的寡唾液酸及其硫代类似物开辟了一条有吸引力的途径。