GlcNAcβ(→14)GlcNAcβNHPr | 1467638-78-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GlcNAcβ(→14)GlcNAcβNHPr
• 英文别名: N-[(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]propanamide
• CAS: 1467638-78-3
• 化学式: C₁₉H₃₃N₃O₁₁
• 分子量: 479.485
• InChiKey: AECHOEPLTPDBQY-JFOOREFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 氨基甲酸铵 作用下， 以 甲醇 为溶剂， 反应 120.0h， 生成 GlcNAcβ(→14)GlcNAcβNHPr
  参考文献：
  名称：

  Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

  摘要：

  The linkage region, GlcNAc beta Asn, is conserved in all eukaryotic N-glycoproteins. As a logical extension of a research endeavor aimed at understanding the structural significance of GlcNAc and Asn as the linkage region constituents, the newer analogs GlcNAc beta NHBu and (GlcNAc beta(1-4)GlcNAc)alkanamides have been synthesized to assess the influence of aglycon as well as additional GlcNAc on the linkage region. X-ray crystallographic analysis of the GlcNAc beta NHBu and (GlcNAc beta(1-4)GlcNAc)beta NHBu is described. Comparative analysis of these structures with those of reported models and analogs shows that the deviation in N-glycosidic torsion, phi(N) among the GlcNAc alkanamides is negligible (<2 degrees) whereas (GlcNAc beta(1-4) GlcNAc)beta NHBu deviates by similar to 15 degrees as compared to GlcNAc beta NHBu. Under the influence of the molecular packing, the conformation around the C1'-C2' bond deviates from anti to gauche in (GlcNAc beta(1-4)GlcNAc beta NHBu. Interestingly, C2-acetamido group in (GlcNAc beta(1-4)GlcNAc)NHBu orients differently as compared to GlcNAc alkanamides and this orientation was found to be almost similar to beta-N,N'-diacetyl-chitobiose trihydrate. The bifurcated anti-parallel pattern involving N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds, a hallmark feature of the N-glycoprotein models, GlcNAc beta NHAc and GlcNAc beta Asn, is absent in both the title alkanamides. This is the first report on the crystal structure analysis of chitobiosyl alkanamide as analog of the N-glycoprotein linkage region, (GlcNAc beta(1-4)GlcNAc)beta Asn. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2013.07.004