N-Acetyl-α-D-arabino-pyranosylamin | 49554-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Acetyl-α-D-arabino-pyranosylamin
• 英文别名: N-[(2S,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]acetamide
• CAS: 49554-40-7
• 化学式: C₇H₁₃NO₅
• 分子量: 191.184
• InChiKey: ZMNJCNGELGRUIX-JWXFUTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-acetyl-2,3,4-tri-O-acetyl-α-D-arabinopyranosylamine 在 barium methoxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以100%的产率得到N-Acetyl-α-D-arabino-pyranosylamin
  参考文献：
  名称：

  Synthesis and X-ray crystallographic investigation of N-(α-d-arabinopyranosyl)alkanamides as N-glycoprotein linkage region analogs

  摘要：

  N-Glycoprotein linkage region constituents namely 2-deoxy-2-acetamido-beta-D-glucopyranose (GlcNAc) and asparagine (Asn) are conserved among all eukaryotes. Earlier crystallographic studies on the linkage region conformation revealed that among all the models and analogs of the N-glycoprotein linkage region, Xyl beta NHAc showed maximum deviation in the phi(N) value as compared to the value reported for the model compound, GlcNAc beta NHAc. In order to understand the effect of another pentopyranose, viz., arabinose, on the N-glycosidic torsion angles and molecular assembly, three arabinopyranosyl alkanamides were synthesized and their X-ray crystal structures elucidated. A comparative analysis of the N-glycosidic torsion, phi(N) of the three analogs revealed the greater rotational freedom around the C1-N1 bond as compared to the GlcNAc derivatives. Molecular assembly of propionamido and chloroacetamido derivatives is characterized by the presence of anti-parallel bilayers of the molecules. This unique molecular assembly is hitherto unknown in all other models and analogs of N-glycoprotein linkage region. This study reveals that N-glycosidic torsions are influenced by the glycan as well as molecular packing. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.014