[(2R,3R,4R,5R)-5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基-四氢呋喃-2-基]甲氧基-[羟基-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-磷酰]氧基-次磷酸 | 5750-57-2

• 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: [(2R,3R,4R,5R)-5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基-四氢呋喃-2-基]甲氧基-[羟基-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-磷酰]氧基-次磷酸
• 中文别名: 1H-吲哚-2,3-二酮,5-溴-7-氟-
• 英文名称: guanosine-5’-diphospho-α-D-glucopyranosyl
• 英文别名: GDP-Glc；Guanosin-diphosphat-glucose；guanosine-5'-diphospho-α-D-glucose；GDP-glucose；O^5'-(2-α-D-glucopyranosyloxy-1,2-dihydroxy-diphosphoryl)-guanosine；diphosphoric acid-1-α-D-glucopyranosyl ester-2-guanosin-5'-yl ester；Diphosphorsaeure-1-α-D-glucopyranosylester-2-guanosin-5'-ylester；[[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-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: 5750-57-2
• 化学式: C₁₆H₂₅N₅O₁₆P₂
• 分子量: 605.346
• InChiKey: MVMSCBBUIHUTGJ-LRJDVEEWSA-N

物化性质

• 密度：
  2.51±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  218.9 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：
  39
• 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：
  327
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  葡萄糖 、 [(2R,3R,4R,5R)-5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基-四氢呋喃-2-基]甲氧基-[羟基-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-磷酰]氧基-次磷酸 在 Pyrococcus horikoshii trehalose synthase 作用下， 反应 24.0h， 生成 海藻糖 、 鸟苷-5’-二磷酸
  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：

  Guanosine 5'-triphosphate 、 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91%的产率得到[(2R,3R,4R,5R)-5-(2-氨基-6-氧代-3H-嘌呤-9-基)-3,4-二羟基-四氢呋喃-2-基]甲氧基-[羟基-[(2R,3R,4S,5R,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基-磷酰]氧基-次磷酸
  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

• Phosphomannose isomerase/GDP-mannose pyrophosphorylase from Pyrococcus furiosus: a thermostable biocatalyst for the synthesis of guanidinediphosphate-activated and mannose-containing sugar nucleotides
  作者：Rahman M. Mizanur、Nicola L. B. Pohl

  DOI：10.1039/b822794b

  日期：——

  Herein we present an analysis of the chemical function of a recombinant bifunctional phosphomannose isomerase/GDP-mannose pyrophosphorylase (manC) from Pyrococcus furiosusDSM 3638 and its use in the synthesis of guanidinediphospho-hexoses and a range of nucleotidediphospho-mannoses. This enzyme is unusually promiscuous in both its nucleotide triphosphate (NTP) and sugar-1-phosphate acceptance. It accepts all five naturally occurring NTPs (ATP, CTP, GTP, dTTP and UTP) and a range of sugar-1-phosphates (glucose-, mannose-, galactose-, glucosamine-, N-acetylglucosamine- and fucose-1-phosphate). A truncated GDP-mannose pyrophosphorylase domain of the whole length enzyme showed almost 100-fold less sugar nucleotidyltransferase activity with only GTP and mannose 1-phosphate as substrates. The temperature stability and inherently broad substrate tolerance of this archaeal enzyme make it an effective reagent for the rapid chemoenzymatic synthesis of a range of natural and unnatural sugar nucleotides that are challenging to make by chemical means alone.

  在本文中，我们分析了来自 Pyrococcus furiosusDSM 3638 的重组双功能磷甘露糖异构酶/GDP-甘露糖焦磷酸化酶（manC）的化学功能，以及它在合成鸟苷酸二磷六糖和一系列核苷酸二磷甘露糖中的应用。这种酶在接受核苷酸三磷酸（NTP）和糖-1-磷酸方面都异常杂乱。它能接受所有五种天然存在的 NTP（ATP、CTP、GTP、dTTP 和 UTP）和一系列糖-1-磷酸（葡萄糖、甘露糖、半乳糖、葡萄糖胺、N-乙酰葡萄糖胺和岩藻糖-1-磷酸）。全长酶的截短 GDP-甘露糖焦磷酸化酶结构域在仅以 GTP 和 1-磷酸甘露糖为底物的情况下，糖核苷酸转移酶活性几乎降低了 100 倍。这种古菌酶的温度稳定性和固有的广泛底物耐受性使其成为一种有效的试剂，可用于快速化学合成一系列天然和非天然糖核苷酸，而这些糖核苷酸很难通过化学方法单独制造。
• Efficient Enzymatic Synthesis of Guanosine 5′-Diphosphate-Sugars and Derivatives
  作者：Lei Li、Yonghui Liu、Yue Wan、Yanhong Li、Xi Chen、Wei Zhao、Peng George Wang

  DOI：10.1021/ol402585c

  日期：2013.11

  Bifidobacterium infantis (NahK_15697), a guanosine 5′-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) were used efficiently for a one-pot three-enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose. This study represents the first facile and efficient enzymatic synthesis of GDP-sugars and derivatives

  来自婴儿双歧杆菌的N-乙酰己糖胺 1-激酶(NahK_15697)、来自激烈火球菌(PFManC)的鸟苷 5'-二磷酸 (GDP)-甘露糖焦磷酸化酶和大肠杆菌无机焦磷酸酶 (EcPpA) 被有效地用于一锅GDP-甘露糖、GDP-葡萄糖及其衍生物和GDP-塔糖的三酶合成。这项研究代表了从单糖和衍生物开始的 GDP 糖和衍生物的首次简便有效的酶促合成。
• 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.