tris((1-(β-D-glucopyranosyl)-1H-[1,2,3]-triazol-4-yl)methyl)amine | 1037821-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tris((1-(β-D-glucopyranosyl)-1H-[1,2,3]-triazol-4-yl)methyl)amine
• 英文别名: (2R,3R,4S,5S,6R)-2-[4-[[bis[[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]triazol-4-yl]methyl]amino]methyl]triazol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1037821-44-5
• 化学式: C₂₇H₄₂N₁₀O₁₅
• 分子量: 746.688
• InChiKey: NCYPSUDABSAKIS-JNILJGCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.5
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  366
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  D-glucopyranosyl azide 、 三炔丙基胺 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 邻苯二胺 作用下， 以 水 为溶剂， 反应 0.75h， 以92%的产率得到tris((1-(β-D-glucopyranosyl)-1H-[1,2,3]-triazol-4-yl)methyl)amine
  参考文献：
  名称：

  Phenylenediamine catalysis of “click glycosylations” in water: practical and direct access to unprotected neoglycoconjugates

  摘要：

  在苷元溶解度允许的情况下，通过苯二胺催化的点击化学反应，可以在纯水中高效、实用、无柱地制备来自未受保护的葡糖基叠氮化物的新苷元共轭物。

  DOI：

  10.1039/b805528a

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。
• A method for labeling specifically living bacteria comprising the use of modified monosaccharide compounds
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2868750A1

  公开（公告）日：2015-05-06

  The invention relates to a method for labeling specifically living bacteria of a given category of Gram negative bacteria in a sample comprising bacteria, the method comprising the steps of: a) incubating said bacteria of said sample with at least one modified monosaccharide compound comprising a first reactive chemical group capable to react with a second reactive group, so that a monosaccharide residue bearing said first reactive group is incorporated into the polysaccharides of the outer membrane of such bacteria, and b) contacting said modified monosaccharide residue incorporated within the outer membrane of the bacteria, with a labeling molecule comprising a said second reactive group. The said modified monosaccharide compound is a compound having the following formula (I), or a salt thereof: Wherein X can be O, NH or S, R1, R2 and R3 can be independently H, OH, NH2, OH and NH2 being substituted or not by protecting groups thereof, and R4 is H or an alkyl chain in C1 to C4 and at least one of X, R1, R2, R3 and R4 groups being substituted by a said first reactive group R'1.

  本发明涉及一种对包含细菌的样品中特定类别的革兰氏阴性活细菌进行标记的方法，该方法包括以下步骤： a) 将所述样品中的细菌与至少一种改性单糖化合物一起培养，该改性单糖化合物包含能与第二反应基团反应的第一反应化学基团，从而使带有所述第一反应基团的单糖残基结合到这些细菌外膜的多糖中，以及 b) 将细菌外膜中的所述改性单糖残基与包含所述第二反应基团的标记分子接触。 所述改性单糖化合物是具有下式 (I) 的化合物或其盐： 其中，X 可以是 O、NH 或 S，R1、R2 和 R3 可以独立地是 H、OH、NH2，OH 和 NH2 是否被其保护基团取代，R4 是 H 或 C1 至 C4 的烷基链，且 X、R1、R2、R3 和 R4 中至少有一个基团被所述第一反应基团 R'1 取代。
• A METHOD FOR LABELING SPECIFICALLY LIVING MICROORGANISMS COMPRISING THE USE OF MODIFIED MONOSACCHARIDE COMPOUNDS
  申请人：Centre National de la Recherche Scientifique (C.N.R.S.)

  公开号：EP3091081A1

  公开（公告）日：2016-11-09

  The invention relates to a method for labeling specifically living microorganisms in a sample comprising microorganisms, the method comprising the steps of: a) incubating said microorganisms of said sample with at least one modified monosaccharide compound comprising a first reactive chemical group capable to chemically react with a second reactive group, so that a residue bearing said first reactive group is incorporated into such microorganisms, and b) contacting said residue incorporated in the microorganisms, with a labeling molecule comprising a said second reactive group, for generating the chemical reaction of said first reactive group of said residue incorporated within said living microorganisms with said second reactive group of said labeling molecule, resulting in a covalent link, characterized in that the said modified monosaccharide compound has the following formula (I'), or a salt thereof: - X can be O, NH or S, preferably O and NH, and - R1 and R2 can be independently H, OH, NH2, OH and NH2 being substituted or not by protecting groups thereof, preferably substituted by alkyl, hydroxyalkyl, acyl, formyl or imidoyl groups, and - R3 is H or an alkyl chain in C1 to C4, each carbon being substituted or not substitued by OH or NH2 substituted or not by protecting groups thereof, preferably by alkyl, hydroxyalkyl, acyl, formyl or imidoyl groups, and - at least one of X, R1, R2 and R3 groups, preferably R3, being substituted by a said first reactive group Ra.

  本发明涉及一种对包含微生物的样品中的活微生物进行特异性标记的方法，该方法包括以下步骤： a) 将所述样品中的微生物与至少一种改性单糖化合物一起培养，该改性单糖化合物包含能与第二活性基团发生化学反应的第一活性化学基团，从而使带有所述第一活性基团的残留物结合到这些微生物中，以及 b) 将微生物中的所述残留物与包含所述第二活性基团的标记分子接触，使活体微生物中的所述残留物的所述第一活性基团与所述标记分子的所述第二活性基团发生化学反应，形成共价连接、 其特征在于，所述改性单糖化合物具有下式（I'）或其盐： - X 可以是 O、NH 或 S，最好是 O 和 NH，以及 - R1 和 R2 可以独立地为 H、OH、NH2，OH 和 NH2 可被或不被其保护基团取代，优选被烷基、羟基烷基、酰基、甲酰基或咪唑酰基取代，以及 - R3 是 H 或 C1 至 C4 的烷基链，每个碳被或未被 OH 或 NH2 取代，被或未被其保护基取代，最好被烷基、羟基烷基、酰基、甲酰基或酰亚胺基取代，以及 - X、R1、R2 和 R3 基团中至少有一个（最好是 R3）被上述第一反应基团 Ra 取代。
• A METHOD FOR LABELING SPECIFICALLY LIVING BACTERIA COMPRISING THE USE OF MODIFIED NON ENDOGENOUS MONOSACCHARIDE COMPOUNDS
  申请人：Centre National de la Recherche Scientifique (C.N.R.S.)

  公开号：EP3091082A1

  公开（公告）日：2016-11-09

  The invention relates to a method for labeling specifically living bacteria, comprising the steps of: a) incubating said bacteria of said sample with at least one modified monosaccharide compound comprising a first reactive chemical group capable to chemically react with a second reactive group, so that a residue bearing said first reactive group is incorporated into the envelope of such bacteria, and b) contacting said modified monosaccharide residue incorporated within the envelope of the bacteria, with a labeling molecule comprising a said second reactive group, for generating the chemical reaction of said first reactive group with said second reactive group, characterized in that said modified monosaccharide compound has the following formula (I), or a salt thereof: Wherein - A, B and C can be independently H, OH, NH2, OH and NH2 being substituted or not by protecting groups thereof, and - D is an alkyl chain in C2 to C4, each carbon being substituted or not by OH or NH2, OH and NH2 being substituted or not by protecting groups thereof, and - at least one of A, B, C or D groups is substituted by a said first reactive group.

  本发明涉及一种标记特定活细菌的方法，包括以下步骤 a) 将所述样品中的细菌与至少一种改性单糖化合物一起培养，该改性单糖化合物包含能与第二反应基团发生化学反应的第一反应基团，从而使带有所述第一反应基团的残留物结合到这种细菌的包膜中，以及 b) 将包含在细菌包膜中的所述改性单糖残基与包含所述第二反应基团的标记分子接触，以产生所述第一反应基团与所述第二反应基团的化学反应、 其特征在于，所述改性单糖化合物具有下式 (I) 或其盐： 其中 - A、B 和 C 可以独立地为 H、OH、NH2，OH 和 NH2 可被或不被其保护基取代，以及 - D 是 C2 至 C4 的烷基链，每个碳可被或不被 OH 或 NH2 取代，OH 和 NH2 可被或不被其保护基取代，以及 - A、B、C 或 D 基团中至少有一个被上述第一反应基团取代。