N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide | 6255-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide
• 英文别名: 2-acetamido-2-deoxy-N-glycyl-β-D-glucopyranosylamine；N-Glycyl-2-acetamino-2-deoxy-β-D-glucosylamin；2-acetamido-2-deoxy-N-glycyl-beta-d-glucopyranosylamine；N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-aminoacetamide
• CAS: 6255-72-7
• 化学式: C₁₀H₁₉N₃O₆
• 分子量: 277.277
• InChiKey: DTVYZCLKXLKNRH-QXOHVQIXSA-N

物化性质

• 沸点：
  719.7±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  154
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Tight binding ligand approach to oligosaccharide-grafted protein

  摘要：

  A novel type of artificial glycoprotein was developed, by using dihydrofolate reductase (DHFR) and methotrexate (MTX) as a protein-ligand pair. Various oligosaccharides linked to MTX were shown to bind tightly with DHFR and afforded oligosaccharide-grafted protein, which could be isolated easily by lectin beads. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.106
• 作为产物：
  描述：

  D-GlcNAc 在 ammonium carbonate 、 碳酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide
  参考文献：
  名称：

  Synthesis ofN4-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues

  摘要：

  N-4-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)-L-aspargine is the principle linkage in the structure of N-linked glycoproteins. Complete assignments of the H-1 and C-13 NMR spectra for three analogues of the naturally-occurring N-glycosylic structure were made for N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)chloroacetamide, N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)bromacetamide and N-1-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)glycinamide. The methylene groups adjacent to the N-glycosylic bond are AB spin systems. Copyright (C) 2001 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1097-458x(200102)39:2<98::aid-mrc792>3.0.co;2-3

文献信息

• N-glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates
  作者：L. M. Likhosherstov、O. S. Novikova、A. O. Zheltova、V. N. Shibaev

  DOI：10.1007/bf02495096

  日期：2000.8

  ofN-glycyl-β-glycopyranosylamines, derivatives of monosaccharides (d-galactose,d-mannose,l-fucose, andN-acetyl-d-glucosamine) and disaccharides (lactose, melibiose, cellobiose, and maltose). These compounds were demonstrated to be useful for the preparation of glycoconjugates of biologically active compounds containing the carboxy group (nicotinic, orotic, kynurenic, and indoleacetic acids). Synthetic pathways

  为合成 N-甘氨酰-β-吡喃葡萄糖胺、单糖衍生物（d-半乳糖、d-甘露糖、l-岩藻糖和 N-乙酰-d-葡糖胺）和二糖（乳糖、蜜二糖、纤维二糖、和麦芽糖）。这些化合物被证明可用于制备含有羧基的生物活性化合物（烟碱酸、乳清酸、犬尿酸和吲哚乙酸）的糖缀合物。开发了使用丙二酸和l-酒石酸衍生物将N-甘氨酰-β-吡喃葡萄糖胺转化为含有羧基的衍生物的合成途径。
• Tight binding ligand approach to oligosaccharide-grafted protein
  作者：Kiichiro Totani、Ichiro Matsuo、Yukishige Ito

  DOI：10.1016/j.bmcl.2004.01.106

  日期：2004.5

  A novel type of artificial glycoprotein was developed, by using dihydrofolate reductase (DHFR) and methotrexate (MTX) as a protein-ligand pair. Various oligosaccharides linked to MTX were shown to bind tightly with DHFR and afforded oligosaccharide-grafted protein, which could be isolated easily by lectin beads. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis ofN4-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues
  作者：Jayshri J. Malik、John M. Risley

  DOI：10.1002/1097-458x(200102)39:2<98::aid-mrc792>3.0.co;2-3

  日期：2001.2

  N-4-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)-L-aspargine is the principle linkage in the structure of N-linked glycoproteins. Complete assignments of the H-1 and C-13 NMR spectra for three analogues of the naturally-occurring N-glycosylic structure were made for N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)chloroacetamide, N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)bromacetamide and N-1-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)glycinamide. The methylene groups adjacent to the N-glycosylic bond are AB spin systems. Copyright (C) 2001 John Wiley & Sons, Ltd.