methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-β-D-glucopyranoside | 1030024-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-β-D-glucopyranoside
• 英文别名: [(2R,3R,4R,5R,6R)-3-acetamido-5-hydroxy-2-methoxy-6-methyloxan-4-yl] acetate
• CAS: 1030024-03-3
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: AJESAEUPOINNFV-WNETWIIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-β-D-glucopyranoside 在 重铬酸吡啶 、 MS 3 Angstroem 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 18.0h， 以60%的产率得到methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-β-D-xylo-hexopyranosid-4-ulose
  参考文献：
  名称：

  Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists

  摘要：

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.001
• 作为产物：
  描述：

  methyl 2-acetamido-2,6-dideoxy-α-D-glucopyranoside 、 乙酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 以40%的产率得到methyl 2-acetamido-3-O-acetyl-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of methyl 2-acetamido-2,6-dideoxy-α- and β-d-xylo-hexopyranosid-4-ulose, a keto sugar which misled the analytical chemists

  摘要：

  To understand the contradictory results on the structure of the lipopolysaccharide isolated from a Yersinia enterocolitica O:3, both anomers of methyl 2-acetamido-2,6-dideoxy-D-xylo-hexopyranosid-4-ulose were prepared. The key steps of the synthetic pathway were the selective acetylation of the methyl 2-acetamido-2,6-dideoxy-alpha,beta-D-glucopyranosides, the oxidation of the 4-position to form the keto-sugars, and deacetylation to provide the target compound. Surprisingly, the last step was accompanied by a disproportionation to give methyl 2-acetamido-2,6-dideoxy-alpha- and beta-D-glucopyranosides and N-(5-hydroxy-6-methyl-4-oxo-4H-pyran-3-yl)acetamide as side-products. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.02.001

文献信息

• Identification and Role of a 6-Deoxy-4-Keto-Hexosamine in the Lipopolysaccharide Outer Core of<i>Yersinia enterocolitica</i>Serotype O:3
  作者：Elise Pinta、Katarzyna A. Duda、Anna Hanuszkiewicz、Zbigniew Kaczyński、Buko Lindner、Wayne L. Miller、Heidi Hyytiäinen、Christian Vogel、Sabine Borowski、Katarzyna Kasperkiewicz、Joseph S. Lam、Joanna Radziejewska-Lebrecht、Mikael Skurnik、Otto Holst

  DOI：10.1002/chem.200901255

  日期：2009.9.28

  The outer core (OC) region of Yersinia enterocolitica serotype O:3 lipopolysaccharide is a hexasaccharide essential for the integrity of the outer membrane. It is involved in resistance against cationic antimicrobial peptides and plays a role in virulence during early phases of infection. We show here that the proximal residue of the OC hexasaccharide is a rarely encountered 4‐keto‐hexosamine, 2‐acetamido‐2

  小肠结肠炎耶尔森氏菌血清型O：3脂多糖的外核（OC）区是六糖，对于外膜的完整性至关重要。它参与了对阳离子抗菌肽的抗性，并在感染的早期阶段发挥了毒性作用。我们在这里展示了OC六糖的近端的残基是很少遇到的4-酮己糖胺，2-乙酰氨基-2,6-二脱氧d -木糖-己-4- ulopyranose（SUG p）和华纳兄弟是UDP -GlcNAC-4,6-脱水酶负责这种罕见糖的核苷酸活化的形式的转换UDP-2-乙酰氨基-2-脱氧生物合成d -glucopyranose（UDP- d -Glc pNAC）到UDP-2-乙酰氨基-2,6-二脱氧d -木糖-己-4- ulopyranose（UDP- SUG p）。在水环境中，由于水合作用，这种糖的4-酮基以4-二羟基形式存在。此外，有证据表明，该二羟基功能的轴向4-羟基对于OC的生物学作用至关重要，即在噬菌体和肠结肠激肽受体结构以及单克隆抗体的表位中至关重要。