D-arabino-hexose-2-ulose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-arabino-hexose-2-ulose
• 英文别名: D-glucosone；(4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,3,4,5-pentol
• 化学式: C₆H₁₂O₇
• 分子量: 196.157
• InChiKey: PMERZXRYEPRZBF-ZRMNMSDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-arabino-hexose-2-ulose 在 sodium hydroxide 、 sodium phosphate 作用下， 生成 2-(二羟基甲基)-2-羟基-2H-吡喃-3(6H)-酮
  参考文献：
  名称：

  Synthesis of the antibiotic cortalcerone from d-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase

  摘要：

  Using two enzymes purified from the white-Tot fungus, PoLyporus obtusus, 5% solutions Of D-glucose have been quantitatively converted in vitro into D-arabino-hexos-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity. The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone. Based on kinetic analysis of the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymically catalyzed steps. Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo. The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase. The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold. Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.

  DOI：

  10.1016/s0008-6215(00)90994-7
• 作为产物：
  描述：

  D-葡萄糖 在 sodium phosphate 、 sodium chloride 作用下， 反应 3.0h， 以95%的产率得到D-arabino-hexose-2-ulose
  参考文献：
  名称：

  Synthesis of the antibiotic cortalcerone from d-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase

  摘要：

  Using two enzymes purified from the white-Tot fungus, PoLyporus obtusus, 5% solutions Of D-glucose have been quantitatively converted in vitro into D-arabino-hexos-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity. The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone. Based on kinetic analysis of the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymically catalyzed steps. Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo. The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase. The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold. Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.

  DOI：

  10.1016/s0008-6215(00)90994-7

文献信息

• COMPOUNDS
  申请人：Costantino Paolo

  公开号：US20130315959A1

  公开（公告）日：2013-11-28

  The invention provides a synthetic C. difficile PS-II cell wall saccharide. The invention also provides a process for purifying C. difficile PS-II saccharide from C. difficile bacterial cells resulting in reduced contamination. The saccharides may be used in vaccines, particularly as conjugates with carrier proteins.

  该发明提供了一种合成的C. difficile PS-II细胞壁多糖。该发明还提供了一种从C. difficile细菌细胞中纯化C. difficile PS-II多糖的方法，从而减少污染。这些多糖可以用于疫苗，特别是作为与载体蛋白结合的共轭物。
• Hydrogenation of crude and purified <scp>d</scp>-glucosone generated by enzymatic oxidation of <scp>d</scp>-glucose
  作者：Robert Lassfolk、Atte Aho、Dmitry Yu. Murzin、Reko Leino

  DOI：10.1039/d0ra05512c

  日期：——

  purified and crude material obtained directly from the enzymatic oxidation, subjected to filtration and lyophilization only. High selectivities towards D-fructose were observed for both starting materials over a Ru/C catalyst. Hydrogenation of the crude D-glucosone was, however, inhibited by the impurities resulting from the enzymatic oxidation process. Catalyst deactivation was observed in the case

  D-果糖是生产糠醛和其他工业重要化学品的重要原料。虽然D-葡萄糖到D-果糖的碱催化和酶促转化是众所周知的，但所采用的方法通常提供有限的转化。D-葡萄糖酮可以通过在C2位酶促氧化从D-葡萄糖中获得，随后在C1位选择性氢化形成D-果糖。这项工作描述了对D-葡萄糖酮氢化的研究，使用色谱纯化和直接从酶氧化获得的粗物质，仅进行过滤和冻干。高选择性在Ru/C催化剂上观察到两种起始材料的D-果糖。然而，粗D-葡萄糖酮的氢化受到酶氧化过程产生的杂质的抑制。在两种起始材料的情况下都观察到催化剂失活。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：NOVARTIS AG

  公开号：WO2012085668A2

  公开（公告）日：2012-06-28

  The invention provides a synthetic C. difficile PS-II cell wall saccharide. The invention also provides a process for purifying C. difficile PS-II saccharide from C. difficile bacterial cells resulting in reduced contamination. The saccharides may be used in vaccines, particularly as conjugates with carrier proteins.
• Synthesis of the antibiotic cortalcerone from d-glucose using pyranose 2-oxidase and a novel fungal enzyme, aldos-2-ulose dehydratase
  作者：Kirston Koths、Robert Halenbeck、Margaret Moreland

  DOI：10.1016/s0008-6215(00)90994-7

  日期：1992.7

  Using two enzymes purified from the white-Tot fungus, PoLyporus obtusus, 5% solutions Of D-glucose have been quantitatively converted in vitro into D-arabino-hexos-2-ulose (D-glucosone) and subsequently into a compound having antimicrobial activity. The antibiotic has been shown by nuclear magnetic resonance and mass spectroscopy to be chemically identical to a previously described fungal metabolite known as cortalcerone. Based on kinetic analysis of the synthetic process, a pathway for the biosynthesis of cortalcerone is proposed, involving both chemical rearrangement and enzymically catalyzed steps. Two enzymes, pyranose 2-oxidase and a previously uncharacterized D-arabino-hexos-2-ulose-utilizing enzyme, may be sufficient for the biosynthesis of cortalcerone from glucose in vivo. The D-arabino-hexos-2-ulose-utilizing enzyme dehydrates certain aldosuloses and has been named aldos-2-ulose dehydratase. The enzyme, which appears to be a dimer of 95-kDa subunits, has been purified 450-fold. Additional properties of aldos-2-ulose dehydratase are described, including its apparent ability to catalyze two different steps in the proposed biosynthetic pathway for cortalcerone.