(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid | 1380545-44-7

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: (2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid
• CAS: 1380545-44-7
• 化学式: C₉₆H₁₆₂N₁₆O₅₇S
• 分子量: 2484.48
• InChiKey: IOKXPSNZMSIGLL-QGCWWOAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -21.1
• 重原子数：
  170
• 可旋转键数：
  56
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  1130
• 氢给体数：
  42
• 氢受体数：
  59

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid 在 3,3,3-膦三基三丙酸 、 谷胱甘肽 、 2,2’-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride 作用下， 反应 6.0h， 以86%的产率得到(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-aminopropanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid
  参考文献：
  名称：

  均质防冻糖肽和糖蛋白的全合成

  摘要：

  不要冻结！天然化学连接-脱硫策略已用于收敛合成大小为1.2至19.5 kDa的确定的抗冻糖肽和糖蛋白（AFGP）库（见图）。这些AFGP具有II型聚脯氨酸螺旋的二级结构，并显示出显着的冰重结晶抑制作用和热滞后活性。

  DOI：

  10.1002/anie.201108682
• 作为产物：
  描述：

  (2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(4R)-1,3-thiazolidine-4-carbonyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid 在 甲氧基胺盐酸盐 作用下， 反应 16.0h， 以81%的产率得到(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoyl]amino]propanoyl]amino]butanoyl]amino]propanoic acid
  参考文献：
  名称：

  均质防冻糖肽和糖蛋白的全合成

  摘要：

  不要冻结！天然化学连接-脱硫策略已用于收敛合成大小为1.2至19.5 kDa的确定的抗冻糖肽和糖蛋白（AFGP）库（见图）。这些AFGP具有II型聚脯氨酸螺旋的二级结构，并显示出显着的冰重结晶抑制作用和热滞后活性。

  DOI：

  10.1002/anie.201108682

文献信息

• Total Synthesis of Homogeneous Antifreeze Glycopeptides and Glycoproteins
  作者：Brendan L. Wilkinson、Robin S. Stone、Chantelle J. Capicciotti、Morten Thaysen-Andersen、Jacqueline M. Matthews、Nicolle H. Packer、Robert N. Ben、Richard J. Payne

  DOI：10.1002/anie.201108682

  日期：2012.4.10

  Don't freeze! A native chemical ligation–desulfurization strategy has been employed for the convergent synthesis of a library of defined antifreeze glycopeptides and glycoproteins (AFGPs) ranging in size from 1.2 to 19.5 kDa (see picture). These AFGPs possessed the secondary structure of a polyproline type II helix and exhibited significant ice recrystallization inhibition and thermal hysteresis activity

  不要冻结！天然化学连接-脱硫策略已用于收敛合成大小为1.2至19.5 kDa的确定的抗冻糖肽和糖蛋白（AFGP）库（见图）。这些AFGP具有II型聚脯氨酸螺旋的二级结构，并显示出显着的冰重结晶抑制作用和热滞后活性。