2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine | 102039-78-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine
• 英文别名: 2-acetamido-4-O-(2-deoxy-β-D-glucopyranosyl)-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine；(GlcNAcβ(1→4)GlcNAc)NHAc；GlcNAc(b1-4)b-GlcNAc1NAc；N-[(2R,3R,4R,5S,6R)-2-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 102039-78-1
• 化学式: C₁₈H₃₁N₃O₁₁
• 分子量: 465.458
• InChiKey: VCXMOKQCWYGNKR-MWKRTYNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine 在 吡啶 作用下， 以33.5 mg的产率得到1-N-acetyl-2-acetamido-2-deoxy-3,6-di-O-acetyl-4-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosylamine
  参考文献：
  名称：

  利用米曲霉和辐射豆的β- N-乙酰己糖胺酶酶促合成N-糖蛋白连接区二糖模拟物

  摘要：

  糖苷酶是用于合成多种二糖和寡糖的有价值的催化剂。本文中，我们报道了N-糖蛋白连接区的简单模型β-1- N-乙酰氨基-2-乙酰氨基-2-脱氧-d-吡喃葡萄糖作为β- N催化的二糖合成的新型受体的用途。-米曲霉和绿豆（Vigna radiata）的α-乙酰己糖胺酶在转糖基化作用下以及逆水解作用下发生。二糖模型，β-d-GlcNAc-（1→4）的专属形成-D-GlcNAcβNHAc，通过转糖和下反转水解相应的（1→6）模拟无论是在合理的产率表明的β-通用性Ñ -乙酰己糖胺酶米曲霉。首次证明了来自Vigna radiata的酶用于合成的功效。这也是关于在糖苷酶催化的逆水解合成模式中使用衍生糖作为共反应物的第一份报告。绿豆β- N-乙酰基己糖胺酶在转糖基作用下的优异选择性（1→6）和米曲霉在逆水解作用下的优异选择性将被证明是非常有用的。

  DOI：

  10.1016/j.tetasy.2004.11.016
• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 ammonium bicarbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 168.0h， 生成 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-1-N-acetyl-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  A new simple synthesis of amino sugar β-d-glycosylamines

  摘要：

  DOI：

  10.1016/0008-6215(86)85037-6

文献信息

• 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
  作者：Manoharan Mathiselvam、Amrita Srivastava、Babu Varghese、Serge Pérez、Duraikkannu Loganathan

  DOI：10.1016/j.carres.2013.07.004

  日期：2013.10

  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.
• New simple synthesis of 2-acetamido-2-deoxy-?-D-glucopyranosylamine and 2-acetamido-4-0-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-2-deoxy-?-D-glucopyranosylamine and preparation of their N-acyl derivatives
  作者：L. M. Likhosherstov、O. S. Novikova、V. A. Derevitskaya、N. K. Kochetkov

  DOI：10.1007/bf00954837

  日期：1986.7