4-keto-D-ribonic acid | 395646-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-keto-D-ribonic acid
• 英文别名: D-erythro-pent-4-ulosonic acid；(2R,3S)-2,3,5-trihydroxy-4-oxopentanoic acid
• CAS: 395646-90-9
• 化学式: C₅H₈O₆
• 分子量: 164.115
• InChiKey: RJALOQXNTCZOJH-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  鸟苷 在 水 作用下， 以 aq. acetate buffer 为溶剂， 反应 16.0h， 生成 4-keto-D-ribonic acid
  参考文献：
  名称：

  Pentose Oxidation by Acetic Acid Bacteria Led to a Finding of Membrane-Bound Purine Nucleosidase

  摘要：

  D-Ribose and 2-deoxy-D-ribose were oxidized to 4-keto-D-ribonate and 2-deoxy-4-keto-D-ribonate respectively by oxidative fermentation, and the chemical structures of the oxidation products were confirmed to be as expected. Both pentoses are important sugar components of nucleic acids. When examined, purine nucleosidase activity predominated in the membrane fraction of acetic acid bacteria. This is perhaps the first finding of membrane-bound purine nucleosidase.

  DOI：

  10.1271/bbb.130066

文献信息

• Enzymatic Synthesis of 4-Pentulosonate (4-Keto-<scp>D</scp>-pentonate) from<scp>D</scp>-Aldopentose and<scp>D</scp>-Pentonate by Two Different Pathways Using Membrane Enzymes of Acetic Acid Bacteria
  作者：Osao ADACHI、Roque A. HOURS、Emiko SHINAGAWA、Yoshihiko AKAKABE、Toshiharu YAKUSHI、Kazunobu MATSUSHITA

  DOI：10.1271/bbb.110575

  日期：2011.12.23

  4-Keto-d-arabonate (d-threo-pent-4-ulosonate) and 4-keto-d-ribonate (d-erythro-pent-4-ulosonate) were prepared from d-arabinose and d-ribose by two successive reactions of membrane-bound enzymes, d-aldopentose 4-dehydrogenase and 4-keto-d-aldopentose 1-dehydrogenase of Gluconobacter suboxydans IFO 12528. Alternatively, they were prepared from d-arabonate and d-ribonate with another membrane-bound enzyme, d-pentonate 4-dehydrogenase. Analytical data confirmed the chemical structures of the 4-pentulosonates prepared. This is the first report of successful enzymatic synthesis of 4-pentulosonates.

  通过膜结合酶（Gluconobacter suboxydans IFO 12528 的 d-aldopentose 4-脱氢酶和 4-keto-d-aldopentose 1-脱氢酶）的两个连续反应，从 d-arabinose 和 d-ribose 制备了 4-Keto-d-arabonate （d-threo-pent-4-ulosonate）和 4-Keto-d-ribonate （d-erythro-pent-4-ulosonate）。另外，它们是用另一种膜结合酶 d-pentonate 4-dehydrogenase 从 d-arabonate 和 d-ribonate 制备的。分析数据证实了所制备的 4-戊酮酸盐的化学结构。这是首次成功用酶合成 4-戊酮酸盐的报道。
• Pentose Oxidation by Acetic Acid Bacteria Led to a Finding of Membrane-Bound Purine Nucleosidase
  作者：Osao ADACHI、Roque A. HOURS、Yoshihiko AKAKABE、Emiko SHINAGAWA、Yoshitaka ANO、Toshiharu YAKUSHI、Kazunobu MATSUSHITA

  DOI：10.1271/bbb.130066

  日期：2013.5.23

  D-Ribose and 2-deoxy-D-ribose were oxidized to 4-keto-D-ribonate and 2-deoxy-4-keto-D-ribonate respectively by oxidative fermentation, and the chemical structures of the oxidation products were confirmed to be as expected. Both pentoses are important sugar components of nucleic acids. When examined, purine nucleosidase activity predominated in the membrane fraction of acetic acid bacteria. This is perhaps the first finding of membrane-bound purine nucleosidase.