尿苷二磷酸酯 2-脱氧葡萄糖 | 6659-40-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 中文名称: 尿苷二磷酸酯 2-脱氧葡萄糖
• 中文别名: 尿苷二磷酸酯2-脱氧葡萄糖
• 英文名称: Uridine diphosphate 2-deoxyglucose
• 英文别名: 2’-deoxy-uridine-5’-diphospho-α-D-glucopyranoside；2'-deoxyuridine-5'-(α-D-glucopyranosyl)diphosphate；dUDP-Glc；diphosphoric acid 1-(2'-deoxy-uridin-5'-yl) ester 2-D-glucopyranosyl ester；2'-Desoxyuridin-diphosphat-glucose；[[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• CAS: 6659-40-1
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: AOQZFKXRCMSXKA-SEKGBAOZSA-N

物化性质

• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  271
• 氢给体数：
  8
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  脱氧尿苷 5'-三磷酸酯 、 对氟苯甲醇 在 Glucose-1-phosphate thymidylyltransferase from Streptococcus pneumonia serotype 23F 、 magnesium chloride 作用下， 反应 1.0h， 以95%的产率得到尿苷二磷酸酯 2-脱氧葡萄糖
  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

• 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。
• Systematic study on the broad nucleotide triphosphate specificity of the pyrophosphorylase domain of the N-acetylglucosamine-1-phosphate uridyltransferase from Escherichia coli K12
  作者：Junqiang Fang、Wanyi Guan、Li Cai、Guofeng Gu、Xianwei Liu、Peng George Wang

  DOI：10.1016/j.bmcl.2009.09.039

  日期：2009.11

  N-Acetylglucosamine-1-phosphate uridyltransferase (GlmU) from Escherichia coli K12 is a bifunctional enzyme that catalyzes both the acetyltransfer and uridyltransfer reactions in the prokaryotic UDP-GlcNAc biosynthetic pathway. In this study, we report the broad substrate specificity of the pyrophosphorylase domain of GlmU during its uridyltransfer reaction and the substrate priority is ranked in the following order: UTP > dUTP > dTTP >> CTP > dATP/dm(6) ATP. This pyrophosphorylase domain of GlmU is also a tool to synthesize UDP-GlcNAc analogs, two examples of which were synthesized herein in multiple mg scale in vitro. (C) 2009 Elsevier Ltd. All rights reserved.
• Biosynthesis of nucleotide sugars by a promiscuous UDP-sugar pyrophosphorylase from Arabidopsis thaliana (AtUSP)
  作者：Jun Liu、Yang Zou、Wanyi Guan、Yafei Zhai、Mengyang Xue、Lan Jin、Xueer Zhao、Junkai Dong、Wenjun Wang、Jie Shen、Peng George Wang、Min Chen

  DOI：10.1016/j.bmcl.2013.04.090

  日期：2013.7

  Nucleotide sugars are activated forms of monosaccharides and key intermediates of carbohydrate metabolism in all organisms. The availability of structurally diverse nucleotide sugars is particularly important for the characterization of glycosyltransferases. Given that limited methods are available for preparation of nucleotide sugars, especially their useful non-natural derivatives, we introduced herein an efficient one-step three-enzyme catalytic system for the synthesis of nucleotide sugars from monosaccharides. In this study, a promiscuous UDP-sugar pyrophosphorylase (USP) from Arabidopsis thaliana (AtUSP) was used with a galactokinase from Streptococcus pneumoniae TIGR4 (SpGalK) and an inorganic pyrophosphatase (PPase) to effectively synthesize four UDP-sugars. AtUSP has better tolerance for C4-derivatives of Gal-1-P compared to UDP-glucose pyrophosphorylase from S. pneumoniae TIGR4 (SpGalU). Besides, the nucleotide substrate specificity and kinetic parameters of AtUSP were systematically studied. AtUSP exhibited considerable activity toward UTP, dUTP and dTTP, the yield of which was 87%, 85% and 84%, respectively. These results provide abundant information for better understanding of the relationship between substrate specificity and structural features of AtUSP. (C) 2013 Elsevier Ltd. All rights reserved.
• A chemoenzymatic route to synthesize unnatural sugar nucleotides using a novel N-acetylglucosamine-1-phosphate pyrophosphorylase from Camphylobacter jejuni NCTC 11168
  作者：Junqiang Fang、Mengyang Xue、Guofeng Gu、Xian-wei Liu、Peng George Wang

  DOI：10.1016/j.bmcl.2013.06.003

  日期：2013.8

  A novel N-acetylglucosamine-1-phosphate pyrophosphorylase was identified from Campylobacter jejuni NCTC 11168. An unprecedented degree of substrate promiscuity has been revealed by systematic studies on its substrate specificities towards sugar-1-P and NTP. The yields of the synthetic reaction of seven kinds of sugar nucleotides catalyzed by the enzyme were up to 60%. In addition, the yields of the other nine were around 20%. With this enzyme, three novel sugar nucleotide analogs were synthesized on a preparative scale and well characterized. (C) 2013 Elsevier Ltd. All rights reserved.