α-D-arabinuronic acid | 134679-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-arabinuronic acid
• 英文别名: (2S,3S,4S,5S)-3,4,5-trihydroxyoxolane-2-carboxylic acid
• CAS: 134679-10-0
• 化学式: C₅H₈O₆
• 分子量: 164.115
• InChiKey: QPIYPWGWBLCOPY-XDBPRBKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基 D-阿糖胞苷 在 platinum(IV) oxide Dowex HCR-W₂ (H⁺) 、 氧气 、 碳酸氢钠 作用下， 以 水 为溶剂， 生成 α-D-arabinuronic acid
  参考文献：
  名称：

  d-Penturonic acids: solution studies of stable-isotopically enriched compounds by 1H- and 13C-n.m.r. spectroscopy

  摘要：

  Methyl D-pentofuranosides were prepared by Fischer glycosidation of the aldopentoses D-arabinose, D-lyxose, D-ribose, D-xylose, and 2-deoxy-D-erythro-pentose, and oxidized with O2 over a platinum oxide catalyst to give the corresponding methyl D-pentofuranosiduronic acids. After purification by anion-exchange chromatography, these glycosides were hydrolyzed to give the corresponding D-penturonic acids [D-arabinuronic acid (1), D-lyxuronic acid (2), D-riburonic acid (3), D-xyluronic acid (4), and 2-deoxy-D-erythro-penturonic acid (5)] in 80% yield based on the starting pentofuranoside. 1-C-13-Substituted D-aldopentoses were used to prepare D-(1-C-13)penturonic acids. Aqueous solutions of the 1-C-13-substituted penturonic acids, studied over a range of pH values by C-13-n.m.r. spectroscopy, were found to contain alpha- and beta-furanoses, acyclic aldehyde and hydrate, and/or hydrated 2,5-lactone. The ratio of D-riburonic acid anomers was most sensitive to solution pH (alpha/beta = 0.49 and 1.2 at pH 1.9 and 4.9, respectively). The values of the H-1 and C-13 chemical shifts, and H-1-H-1, C-13-H-1, and C-13-C-13 spin-coupling constants, were determined by H-1-(300, 500, and 620 MHz) and C-13-(75 MHz) n.m.r. spectroscopy with the aid of 2-D C-13-H-1 chemical shift correlation maps, 2-D H-1-H-1 COSY data, and C-13 substitution, and were compared to those determined previously for structurally-related furanose rings. Isomerization of the penturonic acids at pH 5.0 and 50-degrees gave the corresponding 4-pentulosonic acids.

  DOI：

  10.1016/0008-6215(91)80112-z

文献信息

• d-Penturonic acids: solution studies of stable-isotopically enriched compounds by 1H- and 13C-n.m.r. spectroscopy
  作者：Jian Wu、Anthony S. Serianni

  DOI：10.1016/0008-6215(91)80112-z

  日期：1991.3

  Methyl D-pentofuranosides were prepared by Fischer glycosidation of the aldopentoses D-arabinose, D-lyxose, D-ribose, D-xylose, and 2-deoxy-D-erythro-pentose, and oxidized with O2 over a platinum oxide catalyst to give the corresponding methyl D-pentofuranosiduronic acids. After purification by anion-exchange chromatography, these glycosides were hydrolyzed to give the corresponding D-penturonic acids [D-arabinuronic acid (1), D-lyxuronic acid (2), D-riburonic acid (3), D-xyluronic acid (4), and 2-deoxy-D-erythro-penturonic acid (5)] in 80% yield based on the starting pentofuranoside. 1-C-13-Substituted D-aldopentoses were used to prepare D-(1-C-13)penturonic acids. Aqueous solutions of the 1-C-13-substituted penturonic acids, studied over a range of pH values by C-13-n.m.r. spectroscopy, were found to contain alpha- and beta-furanoses, acyclic aldehyde and hydrate, and/or hydrated 2,5-lactone. The ratio of D-riburonic acid anomers was most sensitive to solution pH (alpha/beta = 0.49 and 1.2 at pH 1.9 and 4.9, respectively). The values of the H-1 and C-13 chemical shifts, and H-1-H-1, C-13-H-1, and C-13-C-13 spin-coupling constants, were determined by H-1-(300, 500, and 620 MHz) and C-13-(75 MHz) n.m.r. spectroscopy with the aid of 2-D C-13-H-1 chemical shift correlation maps, 2-D H-1-H-1 COSY data, and C-13 substitution, and were compared to those determined previously for structurally-related furanose rings. Isomerization of the penturonic acids at pH 5.0 and 50-degrees gave the corresponding 4-pentulosonic acids.