N⁴-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D,L-2-methylsuccinamic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N⁴-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D,L-2-methylsuccinamic acid
• 英文别名: 4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-methyl-4-oxobutanoic acid
• 化学式: C₁₃H₂₂N₂O₈
• 分子量: 334.326
• InChiKey: ARTMEGFGBDVMIF-SCXKVRHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  165
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-GlcNAc 在 ammonium bicarbonate 作用下， 以 水 、 重水 为溶剂， 反应 120.5h， 生成 N⁴-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-D,L-2-methylsuccinamic acid
  参考文献：
  名称：

  SYNTHESIS OFN⁴-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-L-ASPARAGINE ANALOGUES.L-2-CHLORO-,L-2-BROMO-, ANDD,L-2-METHYLSUCCINAMIC ACID ANALOGUES

  摘要：

  L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccinic anhydride react with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine to give varying mixtures of N-4-(beta -GlcNAc)-2-substituted- and N-4-(beta -GlcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are separated by anion exchange chromatography. The N-4-(beta -GlcNAc)-2-substituted-succinamic acid isomers are characterized as analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine.

  DOI：

  10.1081/car-100102542

文献信息

• SYNTHESIS OF<i>N</i>⁴-(2-ACETAMIDO-2-DEOXY-β-<scp>D</scp>-GLUCOPYRANOSYL)-<scp>L</scp>-ASPARAGINE ANALOGUES.<scp>L</scp>-2-CHLORO-,<scp>L</scp>-2-BROMO-, AND<scp>D,L</scp>-2-METHYLSUCCINAMIC ACID ANALOGUES
  作者：Yuan-Qing Xia、John M. Risley

  DOI：10.1081/car-100102542

  日期：2001.2.4

  L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccinic anhydride react with 2-acetamido-2-deoxy-beta -D-glucopyranosylamine to give varying mixtures of N-4-(beta -GlcNAc)-2-substituted- and N-4-(beta -GlcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are separated by anion exchange chromatography. The N-4-(beta -GlcNAc)-2-substituted-succinamic acid isomers are characterized as analogues of N-4-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)-L-asparagine.