D-[1-13C]-glucaric acid | 1185549-29-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-[1-13C]-glucaric acid
• 英文别名: (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy(613C)hexanedioic acid
• CAS: 1185549-29-4
• 化学式: C₆H₁₀O₈
• 分子量: 211.13
• InChiKey: DSLZVSRJTYRBFB-GWGFDAISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  [1-13C]D-glucose 在 硝酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.08h， 生成 D-[1-13C]-glucaric acid
  参考文献：
  名称：

  使用NMR，X射线晶体结构和mm3分子模型分析表征d-葡萄糖酸

  摘要：

  通过比较同位素未标记分子的NMR光谱与氘或碳13原子标记的D-葡糖酸的NMR光谱，可以表征溶液中的​​D-葡糖酸。NMR研究提供了分子的所有碳原子和非羟基质子的明确分配。D-葡糖二酸的晶体结构是通过X射线衍射技术获得的，该结构与使用MM3分子力学程序的基于Monte-Carlo的搜索规程生成的低能构象非常匹配。该分子在晶体和计算产生的最低能量结构中均采用弯曲结构，这种构象没有使蚀变的1,3-羟基相互作用失去稳定性。

  DOI：

  10.1016/j.carres.2011.08.016

文献信息

• Reaction pathways of glucose oxidation by ozone under acidic conditions
  作者：Olivier Marcq、Jean-Michel Barbe、Alain Trichet、Roger Guilard

  DOI：10.1016/j.carres.2009.05.012

  日期：2009.7

  The ozonation Of D-glucose-1-C-13, 2-C-13, and 6-C-13 was carried out at pH 2.5 in a semi-batch reactor at room temperature. The products present in the liquid phase were analyzed by GC-MS, HPAEC-PAD, and C-13 NMR spectroscopy. Common oxidation products of glucose have also been submitted to identical ozonation conditions. For the first time, a pentaric acid was identified and its formation quantitatively correlated to the loss of C-6 of glucose in the form of carbon dioxide. Potential mechanisms for the formation of this pentaric acid are discussed. The well-accepted pathway involving the anomeric position in glucose, gluconic acid, arabinose, and carbon dioxide is reinvestigated. The origin of small molecules such as tartaric, erythronic, and oxalic acids is clarified. Finally, new reaction pathways and tentative mechanisms consistent with the formation of ketoaldonic acids and smaller acids are proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• Characterization of d-glucaric acid using NMR, X-ray crystal structure, and mm3 molecular modeling analyses
  作者：Travis T. Denton、Kenneth I. Hardcastle、Michael K. Dowd、Donald E. Kiely

  DOI：10.1016/j.carres.2011.08.016

  日期：2011.11

  comparing NMR spectra from the isotopically unlabeled molecule with those from D-glucaric acid labeled with deuterium or carbon-13 atoms. The NMR studies provided unequivocal assignments for all carbon atoms and non-hydroxyl protons of the molecule. The crystal structure of D-glucaric acid was obtained by X-ray diffraction techniques and the structure was a close match to the low energy conformation generated

  通过比较同位素未标记分子的NMR光谱与氘或碳13原子标记的D-葡糖酸的NMR光谱，可以表征溶液中的​​D-葡糖酸。NMR研究提供了分子的所有碳原子和非羟基质子的明确分配。D-葡糖二酸的晶体结构是通过X射线衍射技术获得的，该结构与使用MM3分子力学程序的基于Monte-Carlo的搜索规程生成的低能构象非常匹配。该分子在晶体和计算产生的最低能量结构中均采用弯曲结构，这种构象没有使蚀变的1,3-羟基相互作用失去稳定性。