methyl 2-acetamido-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside
• 英文别名: methyl β-D-glucopyranosyluronate-(1→4)-2-(acetylamino)-2-deoxy-α-D-glucopyranoside；GlcA(b1-4)a-GlcNAc1Me；(2S,3S,4S,5R,6R)-6-[(2R,3S,4R,5R,6S)-5-acetamido-4-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₅H₂₅NO₁₂
• 分子量: 411.363
• InChiKey: BFCVSNONBZYERA-WRQXLSPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside 在 硫酸肼 、 肼 作用下， 反应 6.0h， 以85%的产率得到methyl β-D-glucopyranosyluronate-(1→4)-2-amino-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  从N-乙酰基-α-d-葡萄糖胺-O-甲基糖苷受体化学酶法合成硫酸乙酰肝素四糖。

  摘要：

  通过化学酶促合成，在七个步骤中有效地制备了硫酸乙酰肝素四糖2。单糖5，N-乙酰基-α - d-葡糖胺-O-甲基糖苷（GlcNAc-OMe）已成功用作肝素合酶（pmHS2）催化的糖基化反应的受体。这避免了更复杂的二糖受体3的多步合成，大大简化了四糖靶2的路线。该方法为随后的化学酶转化为磺达肝素及其类似物提供了关键的四糖中间体。

  DOI：

  10.1016/j.tetlet.2019.02.036
• 作为产物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 palladium dihydroxide 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hypochlorite 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 1,2,6,6-tetramethylpiperidine-1-oxide 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 硼酸 、 potassium carbonate 、 苄胺 、 三氟乙酸 、 potassium bromide 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 碳酸氢钠 、 N,N-二甲基甲酰胺 为溶剂， 反应 152.0h， 生成 methyl 2-acetamido-2-deoxy-4-O-(β-D-glucopyranosyluronic acid)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of disaccharides derived from heparin and evaluation of effects on endothelial cell growth and on binding of heparin to FGF-2

  摘要：

  The disaccharide beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and other small nonsulfated oligosaccharides related to heparin/heparan sulfate have been shown to bind to FGF and activated the fibroblast growth factor (FGF) signalling pathway in (F32) cells expressing the FGF receptor. Synthetic routes to beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and a glucose analogue beta-D-Glc(1 --> 4)-alpha-D-GlcNAc-1 --> OMe are described. The effects of these disaccharides on endothelial cell growth, which is relevant to angiogenesis, were evaluated and it was found they did not mimic the inhibitory effects that were observed for heparin albumin (HA) and that have also been observed by monosaccharide conjugates. They did not alter bovine aortic endothelial cell (BAEC) proliferation, in the presence of FGF-2 in serum free medium or in absence of FGF-2 in serum free and complete medium. Disaccharides (10 mug/mL) reduced by 25-31% the inhibition caused by HA (10 mug/mL) on BAEC growth in serum-free medium but had no effect in complete medium. There was no evidence obtained for the binding of these oligosaccharides to FGF-2 in competition with HA by ELISA. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.018

文献信息

• Synthesis of disaccharides derived from heparin and evaluation of effects on endothelial cell growth and on binding of heparin to FGF-2
  作者：Alan O’ Brien、Ciaran Lynch、Kathy M. O’ Boyle、Paul V. Murphy

  DOI：10.1016/j.carres.2004.07.018

  日期：2004.10

  The disaccharide beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and other small nonsulfated oligosaccharides related to heparin/heparan sulfate have been shown to bind to FGF and activated the fibroblast growth factor (FGF) signalling pathway in (F32) cells expressing the FGF receptor. Synthetic routes to beta-D-GlcA-(1 --> 4)-alpha-D-GlcNAc-1 --> OMe and a glucose analogue beta-D-Glc(1 --> 4)-alpha-D-GlcNAc-1 --> OMe are described. The effects of these disaccharides on endothelial cell growth, which is relevant to angiogenesis, were evaluated and it was found they did not mimic the inhibitory effects that were observed for heparin albumin (HA) and that have also been observed by monosaccharide conjugates. They did not alter bovine aortic endothelial cell (BAEC) proliferation, in the presence of FGF-2 in serum free medium or in absence of FGF-2 in serum free and complete medium. Disaccharides (10 mug/mL) reduced by 25-31% the inhibition caused by HA (10 mug/mL) on BAEC growth in serum-free medium but had no effect in complete medium. There was no evidence obtained for the binding of these oligosaccharides to FGF-2 in competition with HA by ELISA. (C) 2004 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of heparan sulfate tetrasaccharide from a N-acetyl-α-d-glucosamine-O-methylglycoside acceptor
  作者：Xing Zhang、Demetria M. Dickinson、Lei Lin、Matthew Suflita、Sultan Baytas、Robert J. Linhardt

  DOI：10.1016/j.tetlet.2019.02.036

  日期：2019.3

  Heparan sulfate tetrasaccharide 2 was efficiently prepared in seven steps through chemoenzymatic synthesis. A monosaccharide 5, N-acetyl-α-d-glucosamine- O-methylglycoside (GlcNAc-OMe), was successfully used as an acceptor in a heparosan synthase (pmHS2)-catalyzed glycosylation reaction. This avoided the multi-step synthesis of a more complex disaccharide acceptor 3, greatly simplifying the route to

  通过化学酶促合成，在七个步骤中有效地制备了硫酸乙酰肝素四糖2。单糖5，N-乙酰基-α - d-葡糖胺-O-甲基糖苷（GlcNAc-OMe）已成功用作肝素合酶（pmHS2）催化的糖基化反应的受体。这避免了更复杂的二糖受体3的多步合成，大大简化了四糖靶2的路线。该方法为随后的化学酶转化为磺达肝素及其类似物提供了关键的四糖中间体。