(2S,3S)-3-N-(O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosylcarbamoyl)aziridine-2-carboxylic acid ethyl ester | 1097188-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-3-N-(O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosylcarbamoyl)aziridine-2-carboxylic acid ethyl ester
• 英文别名: ethyl (2S,3S)-3-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl]aziridine-2-carboxylate
• CAS: 1097188-52-7
• 化学式: C₂₂H₃₆N₄O₁₃
• 分子量: 564.547
• InChiKey: YNVHVEBRXICRPF-UMPRCWSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  264
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  ethyl (2S,3S)-3-[[(2R,3R,4R,5S,6R)-5-[[(2R,4aR,6S,7R,8R,8aS)-7-acetamido-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-3-acetamido-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]carbamoyl]aziridine-2-carboxylate 在 palladium hydroxide on carbon 、 氢气 作用下， 以 甲醇 、 2,2,2-三氟乙醇 为溶剂， 以10.46 mg的产率得到(2S,3S)-3-N-(O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosylcarbamoyl)aziridine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Chitobiose-Based Peptide N-Glycanase Inhibitor Library

  摘要：

  Peptide N-glycanase (PNGase), the enzyme responsible for the deglycosylation of N-linked glycoproteins, has an active site related to that of cysteine proteases. Chitiobiose was equipped with electrophilic traps often used in cysteine protease inhibitors, and the resulting compounds were evaluated as PNGase inhibitors. We found that the electrophilic trap of the inhibitor has a great influence on the potency of the compounds with the chloromethyl ketone inhibitor being the first potent C-glycoside-based PNGase inhibitor.

  DOI：

  10.1021/jo801906s

文献信息

• Synthesis and Biological Evaluation of a Chitobiose-Based Peptide <i>N</i>-Glycanase Inhibitor Library
  作者：Martin D. Witte、Danielle Horst、Emmanuel J. H. J. Wiertz、Gijsbert A. van der Marel、Herman S. Overkleeft

  DOI：10.1021/jo801906s

  日期：2009.1.16

  Peptide N-glycanase (PNGase), the enzyme responsible for the deglycosylation of N-linked glycoproteins, has an active site related to that of cysteine proteases. Chitiobiose was equipped with electrophilic traps often used in cysteine protease inhibitors, and the resulting compounds were evaluated as PNGase inhibitors. We found that the electrophilic trap of the inhibitor has a great influence on the potency of the compounds with the chloromethyl ketone inhibitor being the first potent C-glycoside-based PNGase inhibitor.