(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 | 681282-13-3

• 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-[[(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
• CAS: 681282-13-3
• 化学式: C₉₆H₁₆₂N₁₆O₅₇
• 分子量: 2452.42
• InChiKey: SGIMURUZEHFSAG-GRRZJTIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -21
• 重原子数：
  169
• 可旋转键数：
  55
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  1130
• 氢给体数：
  41
• 氢受体数：
  58

反应信息

• 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-[[(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

文献信息

• One-pot synthesis of cyclic antifreeze glycopeptides
  作者：Masakazu Hachisu、Hiroshi Hinou、Manabu Takamichi、Sakae Tsuda、Shuhei Koshida、Shin-Ichiro Nishimura

  DOI：10.1039/b815917c

  日期：——

  The first cyclic glycopeptides exhibiting significant antifreeze activity by forming hexagonal-bipyramidal ice crystals, denoted cyclic antifreeze glycopeptides (cyclic AFGPs), were constructed by a one-pot synthesis based on the controlled cyclization reaction of pre-formed small linear glycopeptides.

  通过形成预形成的小线性糖肽的受控环化反应，通过一锅合成法构建了通过形成六方双锥体冰晶而显示出显着的抗冻活性的第一环状糖肽，即环状抗冻糖肽（环状AFGP）。
• 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。