4,5,6,7,8,9-六羟基-2-氧代-壬酸 | 22594-61-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4,5,6,7,8,9-六羟基-2-氧代-壬酸
• 英文名称: 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid
• 英文别名: ketodeoxynonulosonic acid；Kdn；(4S,5R,6R,7R,8R)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid
• CAS: 22594-61-2
• 化学式: C₉H₁₆O₉
• 分子量: 268.221
• InChiKey: FQHUAUMYHAJTDH-GRCPKETISA-N

物化性质

• 熔点：
  154-162 °C
• 沸点：
  679.7±55.0 °C(Predicted)
• 密度：
  1.722±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  176
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 4,5,6,7,8,9-六羟基-2-氧代-壬酸 在 Dowex-50 (H⁺) 作用下， 反应 48.0h， 以77%的产率得到3-deoxy-D-glycero-β-D-galacto-non-2-ulopyranosonic acid methyl ester
  参考文献：
  名称：

  Studies on Sialic Acid. Part XXVII. Synthesis and Characterization of Furanose and Pyranose Derivatives of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).

  摘要：

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)的费舍尔甲基糖基化产物表明，KDN 的 α, β-呋喃糖和 α, β-吡喃糖之间存在着异构体平衡。尽管存在同分异构平衡，但用乙酸酐与吡啶对 KDN 及其衍生物进行过乙酰化反应只能得到 α 和 β-吡喃糖衍生物。获得的甲基苷和六-O-乙酰基衍生物通过 X 射线、核磁共振和立体二色光谱分析进行了表征。

  DOI：

  10.1248/cpb.40.879

文献信息

• METHOD FOR SPECIFICALLY LABELING LIVING BACTERIA
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：US20140363817A1

  公开（公告）日：2014-12-11

  The present invention concerns a method for labeling specifically living bacteria of a given category in a sample, the method including: a) incubating said bacteria of said sample with at least one analog of a monosaccharide compound, and b) contacting the bacteria with a labeling molecule having a second reactive group.

  本发明涉及一种用于在样品中特异性标记给定类别的活菌的方法，该方法包括：a）将所述样品中的所述菌株与至少一种单糖化合物的类似物一起孵育，并b）将该菌株与具有第二反应性基团的标记分子接触。
• A method for specifically detecting living bacteria
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2617833A1

  公开（公告）日：2013-07-24

  The present invention concerns a method for detecting specifically living bacteria of a given category of bacteria in a sample comprising bacteria, the method comprising the steps of: a) incubating said bacteria of said sample with an analog of a monosaccharide compound, said monosaccharide being an endogenous monosaccharide residue of glycans of the outer membrane of such given category of bacteria, the said endogenous monosaccharide residue comprising an ulosonic acid or ulosonate salt residue, the said analog of a monosaccharide compound being a modified monosaccharide substituted at a given position by a first reactive chemical group capable to react with a second reactive group of a detectable molecule, and b) contacting said bacteria with a said detectable molecule comprising a said second reactive group, for generating the reaction of said first reactive group of said analog residue incorporated within said glycans of the outer membrane of said bacteria with said second reactive group of said detectable, and c) detecting whether said bacteria comprise said detectable molecule bound to the glycans of their outer membrane.

  本发明涉及一种在包含细菌的样品中检测特定类别细菌的方法，该方法包括以下步骤： a) 用单糖化合物类似物培养所述样品中的所述细菌，所述单糖是该类细菌外膜糖的内源性单糖残基、所述内源性单糖残基包括一个溃疡酸或溃疡酸盐残基，所述单糖化合物类似物是在给定位置被能够与可检测分子的第二活性基团反应的第一活性化学基团取代的改性单糖，以及 b) 将所述细菌与包含所述第二活性基团的所述可检测分子接触，以产生包含在所述细菌外膜聚糖中的所述类似残基的所述第一活性基团与所述可检测分子的所述第二活性基团的反应，以及 c) 检测所述细菌的外膜聚糖上是否包含所述可检测分子。
• Kit for labelling bacteria
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：US10571469B2

  公开（公告）日：2020-02-25

  A kit for labeling bacteria, the kit including: an analog of an endogenous monosaccharide residue of glycans of the outer membrane of a given category of bacteria, the endogenous monosaccharide residue being an ulosonic acid or ulosonate salt residue, the analog of a monosaccharide compound being a modified monosaccharide substituted at a given position by a first reactive group capable of reacting with a second reactive group of a labeling molecule; the labeling molecule having the second reactive group capable of reacting with said first reactive group; reactants for generating the reaction of the first reactive group of the analog residue incorporated within the glycans of the outer membrane of the bacteria with the second reactive group of the labeling molecule; and a culture or incubation medium allowing growth of the given category of bacteria, specific to the growth of the given category of bacteria.

  用于标记细菌的试剂盒，试剂盒包括 一种特定类别细菌外膜聚糖的内源性单糖残基的类似物，该内源性单糖残基是一种乌洛托品酸或乌洛托品酸盐残基，该单糖化合物类似物是一种在特定位置被能够与标记分子的第二反应基团反应的第一反应基团取代的改性单糖； 具有能与所述第一反应基团反应的第二反应基团的标记分子； 反应物，用于使加入细菌外膜聚糖中的模拟残基的第一反应基团与标记分子的第二反应基团发生反应；以及 允许特定种类细菌生长的培养基或孵育培养基，专门用于特定种类细菌的生长。
• Two-Step Chemoenzymatic Detection of <i>N</i>-Acetylneuraminic Acid−α(2-3)-Galactose Glycans
  作者：Liuqing Wen、Yuan Zheng、Kuan Jiang、Mingzhen Zhang、Shukkoor Muhammed Kondengaden、Shanshan Li、Kenneth Huang、Jing Li、Jing Song、Peng George Wang

  DOI：10.1021/jacs.6b07132

  日期：2016.9.14

  Sialic acids are typically linked alpha(2-3) or alpha(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-alpha(2-3)-galactose glycans is described.
• A METHOD FOR SPECIFICALLY LABELING LIVING BACTERIA
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2804953B1

  公开（公告）日：2015-10-28