腺苷焦磷酸酯-葡萄糖 | 2140-58-1

• 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
• 中文名称: 腺苷焦磷酸酯-葡萄糖
• 英文名称: adenosine-5'-(α-D-glucopyranosyl)diphosphate
• 英文别名: adenosine-5'-diphospho-α-D-glucose；adenosine-5'-diphosphoglucose；ADP-α-D-glucose；ADP-Glc；ADP-glucose；O^5'-(2-glucopyranosyloxy-1,2-dihydroxy-phosphoryl)-adenosine；[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• CAS: 2140-58-1
• 化学式: C₁₆H₂₅N₅O₁₅P₂
• 分子量: 589.347
• InChiKey: WFPZSXYXPSUOPY-ROYWQJLOSA-N

物化性质

• 沸点：
  997.5±75.0 °C(Predicted)
• 密度：
  2.42±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  214.5 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  312
• 氢给体数：
  9
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  腺苷焦磷酸酯-葡萄糖 在 Pyrococcus horikoshii trehalose synthase 作用下， 反应 48.0h， 生成 葡萄糖
  参考文献：
  名称：

  Catalytic reversibility of Pyrococcus horikoshii trehalose synthase: Efficient synthesis of several nucleoside diphosphate glucoses with enzyme recycling

  摘要：

  The trehalose synthase (TreT) from Pyrococcus horikoshii represented reversible catalysis in alternative synthesis of trehalose and nucleoside 5'-diphosphate-glucose (NDP-Glc), depending on the substrates involved. TreT from P. horikoshii had differential preferences on NDP-Glc as a donor for trehalose synthesis, in which guanosine 5'-diphosphate (GDP)-Glc was the most favored in terms of reaction specificity, k(cat)/K-m. Uridine 5'-diphosphate (UDP)- and adenosine 5'-diphosphate (ADP)-Glcs were employed with less preferences. This enzyme reversely cleaved trehalose to transfer the glucosyl moiety to various NDPs, efficiently producing NDP-Glcs. Although ADP-Glc was the least favorable donor, the counterpart, ADP, was the most favorable acceptor for the reverse synthesis of NDP-Glc in k(cat)/K-m. GDP and UDP were less preferred, compared to ADP. In a batch reaction of 12 h, the molar yield of NDP-Glc per NDP used was decreased approximately in the order of ADP-Glc > GDP-Glc > cytidine 5'-diphosphate (CDP)-Glc or UDP-Glc. The overall productivity of the enzyme was largely improved in a gram scale for NDP-Glcs using repetitive batch reactions with enzyme recycling. Thus, it is suggested that TreT from P. horikoshii may be useful for the regeneration of NDP-Glc from NDP, especially for ADP-Glc from ADP, with trehalose as a glucose resource. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.procbio.2010.07.030
• 作为产物：
  描述：

  5’-三磷酸腺苷 、 对氟苯甲醇 在 Glucose-1-phosphate thymidylyltransferase from Streptococcus pneumonia serotype 23F 、 magnesium chloride 作用下， 反应 6.0h， 以78%的产率得到腺苷焦磷酸酯-葡萄糖
  参考文献：
  名称：

  探索肺炎链球菌血清型 23F 胸苷转移酶 Cps23FL 的宽核苷酸三磷酸和糖 1-磷酸特异性

  摘要：

  来自肺炎链球菌血清型 23F 的葡萄糖-1-磷酸胸苷转移酶 (Cps23FL)是在原核脱氧胸苷二磷酸-L-鼠李糖 (dTDP-Rha) 生物合成途径中催化胸苷转移反应的初始酶。在这项研究中，系统地探索了 Cps23FL 对六种葡萄糖 1-磷酸和九种三磷酸核苷作为底物的广泛底物特异性，最终提供了对 19 种糖核苷酸类似物的访问。

  DOI：

  10.1039/d0ra05799a

文献信息

• Stereospecific synthesis of sugar-1-phosphates and their conversion to sugar nucleotides
  作者：Shannon C. Timmons、David L. Jakeman

  DOI：10.1016/j.carres.2008.01.046

  日期：2008.4

  products, efficient access to stereopure sugar nucleotide donor substrates is required. Herein, the rapid synthesis and purification of eight sugar nucleotides is described by a facile 30 min activation of nucleoside 5'-monophosphates bearing purine and pyrimidine bases with trifluoroacetic anhydride and N-methylimidazole, followed by a 2 h coupling with stereospecifically prepared sugar-1-phosphates. Tributylammonium

  随着Leloir糖基转移酶越来越多地用于制备寡糖，糖结合物和糖基化天然产物，需要有效地获得立体纯糖核苷酸供体底物。本文中，通过用三氟乙酸酐和N-甲基咪唑将带有嘌呤和嘧啶碱基的核苷5'-单磷酸核苷轻松活化30分钟，然后与立体定向制备的糖-1偶联2小时，从而快速合成和纯化八个糖核苷酸-磷酸盐。碳酸氢三丁铵和乙酸三丁铵是分别用于6-脱氧糖核苷酸和己糖或戊糖衍生糖核苷酸的C18反相纯化的离子对试剂。
• Combined enzymatic synthesis of nucleotide (deoxy) sugars from sucrose and nucleoside monophosphates
  作者：Astrid Zervosen、Andreas Stein、Holger Adrian、Lothar Elling

  DOI：10.1016/0040-4020(95)01081-5

  日期：1996.2

  The synthesis of NDP-glucose 3a-d (NA, C, U, dU) with sucrose synthase B was combined with the enzymatic synthesis of nucleoside diphosphates 2a-d from their corresponding nucleoside monophosphates 1a-d by different kinases A. Further combination with recombinant dTDP-glucose 4,6-dehydratase D enabled us to synthesize dUDP-6-deoxy-α-D-xylo-4-hexulose 5 from 1d on a preparative scale. By using the

  用蔗糖合酶B合成NDP-葡萄糖3a-d（NA，C，U，dU）与通过不同的激酶A从其相应的核苷单磷酸1a-d酶促合成核苷二磷酸2a-d。与重组dTDP-葡萄糖4,6-脱水酶D的进一步结合使我们能够按制备规模从1d合成dUDP-6-脱氧-α-D-木糖-4-己糖5。通过使用重复批处理技术，核苷酸（脱氧）糖3a-d，5的酶促合成可以在0.1 – 0.5 g的范围内进行。
• Exploiting Nucleotidylyltransferases To Prepare Sugar Nucleotides
  作者：Shannon C. Timmons、Roy H. Mosher、Sheryl A. Knowles、David L. Jakeman

  DOI：10.1021/ol0630853

  日期：2007.3.1

  Enzymatic approaches to prepare sugar nucleotides are gaining in importance and offer several advantages over chemical synthesis including high yields and stereospecificity. We report the cloning, expression, and purification of two new wild-type thymidylyltransferases and observed catalysis with a wide variety of substrates. Significant product inhibition was not observed with the enzymes studied over a 24 h period, enabling the efficient preparation of 15 sugar nucleotides, clearly demonstrating the synthetic utility of these biocatalysts.
• Ectopic Expression of Anthocyanin 5-<i>O</i>-Glucosyltransferase in Potato Tuber Causes Increased Resistance to Bacteria
  作者：Katarzyna Lorenc-Kukuła、Sylwia Jafra、Jan Oszmiański、Jan Szopa

  DOI：10.1021/jf048449p

  日期：2005.1.1

  The principal goal of this paper was to investigate the significance of anthocyanin 5-O-glucosyltransferase (5-UGT) for potato tuber metabolism. The ectopic expression of a 5-UGT cDNA in the tuber improved the plant's defense against pathogen infection. The resistance of transgenic lines against Erwinia carotovora subsp. carotovora was about 2-fold higher than for nontransformed plants. In most cases the pathogen resistance was accompanied by a significant increase in tuber yield. To investigate the molecular basis of transgenic potato resistance, metabolic profiling of the plant was performed. In tuber extracts, the anthocyanin 3,5-O-substituted level was significantly increased when compared to that of the control plant. Of six anthocyanin compounds identified, the highest quantity for pelargonidin 3-rutinoside-5-glucoside acylated with p-coumaric acid and peonidin 3-rutinoside-5-glucoside acylated with p-coumaric acid was detected. A significant increase in starch and a decrease in sucrose level in transgenic tubers have been detected. The level of all other metabolites (amino acids, organic acids, polyamines, and fatty acids) was quite the same as in nontransformants. The plant resistance to bacterial infection correlates with anthocyanin content and sucrose level. The properties of recombinant glucosyltransferase were analyzed in in vitro experiments. The enzyme kinetics and its biochemical properties were similar to those from other sources.
• US6103893A
  申请人：——

  公开号：US6103893A

  公开（公告）日：2000-08-15