2,3-Dihydroxybenzoyl 5'-adenylate | 122408-18-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 2,3-Dihydroxybenzoyl 5'-adenylate
• 英文别名: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2,3-dihydroxybenzoate
• CAS: 122408-18-8
• 化学式: C₁₇H₁₈N₅O₁₀P
• 分子量: 483.331
• InChiKey: ULPVJDOMCRTJSN-RVXWVPLUSA-N

物化性质

• 沸点：
  886.9±75.0 °C(Predicted)
• 密度：
  2.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  233
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  苯甲酸,二羟基- 、 5’-三磷酸腺苷 在 sodium chloride 、 bovine serum albumin 作用下， 以 aq. buffer 为溶剂， 生成 2,3-Dihydroxybenzoyl 5'-adenylate
  参考文献：
  名称：

  通过酵母细胞表面展示设计 DhbE 腺苷酸化域的底物特异性

  摘要：

  非核糖体肽合成酶 (NRPS) 的腺苷酸化 (A) 结构域激活芳酸或氨基酸，以通过 NRPS 装配线启动它们的转移，用于生物合成许多具有药用价值的天然产物。为了扩大 NRPS 的底物池，我们开发了一种基于酵母细胞表面展示的方法来设计 A 域的底物特异性。我们获得了 DhbE 的 A 域突变体，这些突变体分别使非天然底物 3-羟基苯甲酸和 2-氨基苯甲酸的inkcat/Km 增加了 11 倍和 6 倍，并且使用天然底物 2 时相应的inkcat/Km 值降低了 3 倍和 33 倍,3-二羟基苯甲酸，导致底物特异性的显着变化高达 200 倍。

  DOI：

  10.1016/j.chembiol.2012.10.020

文献信息

• ANTI-MICROBIAL AGENTS AND USES THEREOF
  申请人：Tan Derek Shieh

  公开号：US20090170805A1

  公开（公告）日：2009-07-02

  Many pathogens, including Mycobacterium tuberculosis and Yersinia pestis , rely on an iron acquisition system based on siderophores, secreted iron-chelating compounds with extremely high Fe(III) affinity. The compounds of the invention are inhibitors of domain salicylation enzymes, which catalyze the salicylation of an aroyl carrier protein (ArCP) domain to form a salicyl-ArCP domain thioester intermediate via a two-step reaction. The compounds include the intermediate mimic 5′-O—[N-(salicyl)sulfamoyl]-adenosine (salicyl-AMS) and analogs thereof. These compounds are inhibitors of the salicylate activity of MbtA, YbtE, PchD, and other domain salicylation enzymes involved in the biosynthesis of siderophores. Therefore, these compounds may be used in the treatment of infection caused by microorganisms which rely on siderphore-based iron acquisition systems. Pharmaceutical composition and methods of using these compounds to treat or prevent infection are also provided as well as methods of preparing the inventive compounds.
• Probe Compound for Detecting and Isolating Enzymes and Means and Methods Using the Same
  申请人：Golyshin Peter N.

  公开号：US20120231972A1

  公开（公告）日：2012-09-13

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• [EN] PROBE COMPOUND FOR DETECTING AND ISOLATING ENZYMES AND MEANS AND METHODS USING THE SAME<br/>[FR] COMPOSÉ SONDE POUR DÉTECTER ET ISOLER DES ENZYMES ET MOYENS ET PROCÉDÉS POUR L'UTILISER
  申请人：HELMHOLTZ INFEKTIONSFORSCHUNG

  公开号：WO2010105851A1

  公开（公告）日：2010-09-23

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.
• Engineering the Substrate Specificity of the DhbE Adenylation Domain by Yeast Cell Surface Display
  作者：Keya Zhang、Kathryn M. Nelson、Karan Bhuripanyo、Kimberly D. Grimes、Bo Zhao、Courtney C. Aldrich、Jun Yin

  DOI：10.1016/j.chembiol.2012.10.020

  日期：2013.1

  the substrate pool of NRPSs, we developed a method based on yeast cell surface display to engineer the substrate specificities of the A-domains. We acquired A-domain mutants of DhbE that have 11- and 6-fold increases inkcat/Kmwith nonnative substrates 3-hydroxybenzoic acid and 2-aminobenzoic acid, respectively and corresponding 3- and 33-fold decreases inkcat/Kmvalues with the native substrate 2,3-dihydroxybenzoic

  非核糖体肽合成酶 (NRPS) 的腺苷酸化 (A) 结构域激活芳酸或氨基酸，以通过 NRPS 装配线启动它们的转移，用于生物合成许多具有药用价值的天然产物。为了扩大 NRPS 的底物池，我们开发了一种基于酵母细胞表面展示的方法来设计 A 域的底物特异性。我们获得了 DhbE 的 A 域突变体，这些突变体分别使非天然底物 3-羟基苯甲酸和 2-氨基苯甲酸的inkcat/Km 增加了 11 倍和 6 倍，并且使用天然底物 2 时相应的inkcat/Km 值降低了 3 倍和 33 倍,3-二羟基苯甲酸，导致底物特异性的显着变化高达 200 倍。