4-keto-D-ribose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-keto-D-ribose
• 英文别名: D-erythro-[4]pentosulose；D-erythro-Pentos-4-ulose；(2R,3S)-2,3,5-trihydroxy-4-oxopentanal
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: XIIKTJZKWRJKSI-UCORVYFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  10
• 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：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D-核糖 在 Gluconobacter suboxydans IFO 12528 membrane fraction 作用下， 以 水 为溶剂， 生成 4-keto-D-ribose 、 4-keto-D-ribonic acid
  参考文献：
  名称：

  Enzymatic Synthesis of 4-Pentulosonate (4-Keto-D-pentonate) fromD-Aldopentose andD-Pentonate by Two Different Pathways Using Membrane Enzymes of Acetic Acid Bacteria

  摘要：

  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。

  DOI：

  10.1271/bbb.110575

文献信息

• Photoionization of Organic Phosphates by 193 nm Laser Light in Aqueous Solution:  Rapid Intramolecular H-Transfer to the Primarily Formed Phosphate Radical. A Model for Ionization-Induced Chain-Breakage in DNA?
  作者：Steen Steenken、Ludmila Goldbergerova

  DOI：10.1021/ja974393m

  日期：1998.4.1

  phosphates such as ribose-5-phosphate leads to ionization with formation of the corresponding oxygen-centered phosphate radicals, O3PO•. These (oxidizing) radicals function as traps with respect to hydrogens attached to α-, β-, or, possibly, γ-carbons, whereby in the case of the β-hydrogens a six-membered transition state for transfer of the hydrogen to the phosphate oxygen is possible, leading to high rate

  在水溶液中，193 nm (6.4 eV) 无机和有机磷酸盐（如 5-磷酸核糖）的光解导致电离，形成相应的以氧为中心的磷酸根 O3PO•。这些（氧化）自由基对于连接到 α-、β- 或可能的 γ-碳上的氢起到陷阱的作用，其中在 β-氢的情况下，六元过渡态用于将氢转移到磷酸氧是可能的，导致这些单分子反应中氢转移的高速率常数（高达> 5 × 107 s-1）。在（脱氧）核糖磷酸酯的情况下，六元过渡态有可能将 C4 的氢转移到 C5 和 C3 的磷酸基团。在 DNA 中，由此产生的 C4'-自由基将经历磷酸酯基团的快速β-消除，这一步代表 DNA 链断裂。显然很容易从碳到磷酸根的 H 转移，这些自由基被“修复”，这就是为什么磷酸根不...
• 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.
• 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。