4-氨基甲酰基苯胺甲酸琥珀酰亚胺酯 | 200197-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基甲酰基苯胺甲酸琥珀酰亚胺酯
• 英文名称: 4-carbamoyl-phenylcarbamic acid 2,5-dioxopyrrolidin-1-yl ester
• 英文别名: 2,5-dioxo-pyrrolidin-1-yl 4-carbamoyl-phenylcarbamate；4-aminobenzamidyI-N-hydroxysuccinimidyl carbamate；2,5-Dioxopyrrolidin-1-yl (4-carbamoylphenyl)carbamate；(2,5-dioxopyrrolidin-1-yl) N-(4-carbamoylphenyl)carbamate
• CAS: 200197-04-2
• 化学式: C₁₂H₁₁N₃O₅
• 分子量: 277.236
• InChiKey: VXXQVFDQGVJZNL-UHFFFAOYSA-N

物化性质

• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5R)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-6-sulfonic acid 、 4-氨基甲酰基苯胺甲酸琥珀酰亚胺酯 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以78%的产率得到Sodium; (1S,5R)-2-(4-carbamoyl-phenylcarbamoyl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-6-sulfonate
  参考文献：
  名称：

  Structure-Based Design of β-Lactamase Inhibitors. 1. Synthesis and Evaluation of Bridged Monobactams

  摘要：

  Bridged monobactams are novel, potent, mechanism-based inhibitors of class C beta-lactamases, designed using X-ray crystal structures of the enzymes. They stabilize the acyl-enzyme intermediate by blocking access of water to the enzyme-inhibitor ester bond. Bridged monobactams are selective class C beta-lactamase inhibitors, with half-inhibition constants as low as 10 nM, and are less effective against class A and class B enzymes (half-inhibition constants > 100 mu M) because of the different hydrolysis mechanisms in these classes of beta-lactamases. The stability of the acyl-enzyme complexes formed with class C beta-lactamases (half-lives up to 2 days were observed) enabled determination of their crystal structures. The conformation of the inhibitor moiety was close to that predicted by molecular modeling, confirming a simple reaction mechanism, unlike those of known beta-lactamase inhibitors such as clavulanic acid and penam sulfones, which involve secondary rearrangements. Synergy between the bridged monobactams and beta-lactamase-labile antibiotics could be observed when such combinations were tested against strains of Enterobacteriaceae that produce large amounts of class C beta-lactamases. The minimal inhibitory concentration of the antibiotic of more than 64 mg/L could be decreased to 0.25 mg/L in a 1:4 combination with the inhibitor.

  DOI：

  10.1021/jm980023c
• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 对氨基苯甲酰胺 以 乙腈 为溶剂， 以80%的产率得到4-氨基甲酰基苯胺甲酸琥珀酰亚胺酯
  参考文献：
  名称：

  [EN] COMPOUNDS AND METHODS FOR RAPID LABELING OF N-GLYCANS
  [FR] COMPOSITIONS ET PROCÉDÉS POUR LE MARQUAGE RAPIDE DE N-GLYCANES

  摘要：

  本发明提供了化合物和方法，用于快速标记N-糖基，例如，快速荧光标记N-糖基。在一个方面，本发明提供了荧光氨基甲酸酯或硫氨基甲酸酯化合物。与N-糖基接触后，这些化合物与N-糖基发生简便的反应，形成荧光标记的N-糖基。

  公开号：

  WO2009100155A1

文献信息

• [EN] COMPOUNDS AND METHODS FOR RAPID LABELING OF N-GLYCANS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR LE MARQUAGE RAPIDE DE N-GLYCANES
  申请人：PROZYME INC

  公开号：WO2009100155A1

  公开（公告）日：2009-08-13

  The present invention provides compounds and methods for rapid labeling of N-glycans, for example, rapid fluorescent labeling of N-glycans. In one aspect, the present invention provides fluorescent carbamate or thiocarbamate compounds. Upon contacting with N-glycans, the compounds undergo facile reactions with N-glycans to form fluorescent-labeled N-glycans.

  本发明提供了化合物和方法，用于快速标记N-糖基，例如，快速荧光标记N-糖基。在一个方面，本发明提供了荧光氨基甲酸酯或硫氨基甲酸酯化合物。与N-糖基接触后，这些化合物与N-糖基发生简便的反应，形成荧光标记的N-糖基。
• Tricyclic carbacephems
  申请人：Hoffmann-la Roche Inc.

  公开号：US06218379B1

  公开（公告）日：2001-04-17

  The present invention is concerned with compounds of formula where A is a group of formula (b1) or (b2) where R3 is unsubstituted aryl or aryl substituted by one or two substituents defined herein, and R is as defined herein, together with the pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds. These compounds have valuable antibacterial properties.

  本发明涉及以下化合物的公式，其中A是公式（b1）或（b2）的基团，其中R3是未取代的芳基或芳基，其由本处定义的一个或两个取代基取代，R如本处定义，以及这些化合物的药用兼容、易水解的酯和盐。这些化合物具有宝贵的抗菌性能。
• .beta.-lactam compounds
  申请人：Hoffmann-La Roche Inc.

  公开号：US05464617A1

  公开（公告）日：1995-11-07

  Compounds of the formula ##STR1## where Z, A, and R are as disclosed herein and pharmaceutically compatible, readily hydrolyzable esters and salts of these compounds are disclosed. The compounds have .beta.-lactamase inhibiting properties and are useful in the control of .beta.-lactamase-forming pathogens in combination with .beta.-lactam antibiotics. They also exhibit antibacterial activity of their own and can accordingly be used themselves in the control or treatment of infectious diseases.

  这些化合物的分子式为##STR1##其中Z、A和R如本文所披露的，这些化合物的药用兼容、易水解的酯和盐也被披露。这些化合物具有β-内酰胺酶抑制特性，并可与β-内酰胺类抗生素结合使用，用于控制β-内酰胺酶形成的病原体。它们还表现出自身的抗菌活性，因此可以单独用于控制或治疗传染病。
• METHODS FOR THE RAPID PREPARATION OF LABELED GLYCOSYLAMINES AND FOR THE ANALYSIS OF GLYCOSYLATED BIOMOLECULES PRODUCING THE SAME
  申请人：Waters Technologies Corporation

  公开号：EP3748340A1

  公开（公告）日：2020-12-09

  Methods of analyzing glycosylated biomolecules include the steps of producing a deglycosylation mixture of biomolecules deglycosylated by natural or synthetic enzymatic or chemical techniques; providing a reagent solution having a labeling reagent in a polar aprotic, non-nucleophilic organic solvent; and mixing the deglycosylation mixture with the reagent solution in an excess of labeling reagent to produce derivatized glycosylamines. The method steps can be carried out purposefully without depletion of protein matter. A quenching solution can be added to the reaction mixture so that the pH of the reaction mixture is shifted to above 10. The yield of derivatized glycosylamines can be in an amount of about 80 to about 100 mole percent of the reaction mixture with minimal overlabeling, less than 0.2 mole percent. The derivizated glycosylamines can be separated from the reaction mixture and detected by chromatographic detection, fluorescence detection, mass spectrometry ("MS"), or Ultra Violet ("UV") detection and/or a combination thereof.

  分析糖基化生物大分子的方法包括以下步骤：制备由天然或合成酶或化学技术脱糖的生物大分子组成的脱糖混合物；在极性非亲核有机溶剂中提供具有标记试剂的试剂溶液；以及将脱糖混合物与标记试剂过量的试剂溶液混合，生成衍生化的糖基化胺。这些方法步骤可以在不损耗蛋白质物质的情况下有目的地进行。可向反应混合物中加入淬灭溶液，使反应混合物的 pH 值升至 10 以上。衍生化糖基胺的产率可达到反应混合物的约 80 至约 100 摩尔%，且重叠标记最小，小于 0.2 摩尔%。衍生化的糖基胺可以从反应混合物中分离出来，并通过色谱检测、荧光检测、质谱（"MS"）或紫外线（"UV"）检测和/或它们的组合进行检测。
• CALIBRANT FOR LIQUID CHROMATOGRAPHY CALIBRATION OF LABELED N-GLYCANS
  申请人：Waters Technologies Corporation

  公开号：EP3744708A1

  公开（公告）日：2020-12-02

  Methods are provided for making rapid labeled dextran ladders and other calibrants useful in liquid chromatography. The methodologies include a two-step process comprising a reductive amination step of providing a reducing glycan and reacting it with a compound having a primary amine to produce an intermediate compound. The intermediate compound is then rapidly tagged with a rapid tagging reagent to produce the rapid labeled dextran ladder.

  本发明提供了用于液相色谱法中的快速标记葡聚糖阶梯和其他校准物的制造方法。这些方法包括一个还原胺化步骤和两个步骤，还原胺化步骤是提供还原性聚糖并使其与具有伯胺的化合物反应生成中间化合物。然后用快速标记试剂对中间化合物进行快速标记，生成快速标记葡聚糖梯形图。