尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 | 133-89-1

• 物质功能分类: 生物化工 - 糖类化合物
• 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(5')二氢二磷酰(1)-alpha-D-葡萄糖
• 中文别名: UDP-葡萄糖；5'-三磷酸氢-β-D-吡喃葡萄糖尿苷
• 英文名称: UDP-glucose
• 英文别名: uridine diphosphate glucose；UDPG；UDP-Glc；UDP-α-D-glucose；UDP-D-glucose；Uridine-5'-diphosphate-glucose；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-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: 133-89-1
• 化学式: C₁₅H₂₄N₂O₁₇P₂
• 分子量: 566.306
• InChiKey: HSCJRCZFDFQWRP-JZMIEXBBSA-N

物化性质

• 溶解度：
  Easily soluble (water), soluble (methanol), insoluble ((CH3)2CO, (C2H5)2O)
• 密度：
  1.97±0.1 g/cm3(Predicted)
• 物理描述：
  Solid
• 碰撞截面：
  209.2 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  36
• 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：
  292
• 氢给体数：
  9
• 氢受体数：
  17

安全信息

• 储存条件：
  | 2-8℃ |

制备方法与用途

UDP-葡萄糖是一种核苷酸糖，涉及代谢过程中糖基转移酶的反应。它是糖原的前体，并可转化为半乳糖和UDP-葡糖醛酸，进而通过酶作用生成含有半乳糖和葡糖醛酸的多糖。

除了作为代谢过程中的重要参与者外，UDP-葡萄糖还可作为脂多糖和鞘糖脂的前体。

Uridine diphosphate glucose (UDPG) 是动物组织和某些微生物中含有葡萄糖的寡糖、多糖、糖蛋白和糖脂的前体。此外，它还是一种P2Y14受体（一种神经免疫系统中的G蛋白偶联受体）激动剂。

人类内源代谢物

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 α(1->4) galactosyltransferase α(1->4)galactosyltransferase from N. meningitidis 、 β(1->3)N-acetylgalactosaminyltransferase-WbgU fusion enzyme 、 GalE from Escherichia coli K₁₂ 、 manganese(ll) chloride 、 bovine serum albumin 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 生成 β-D-N-acetyl-galactosaminyl-(1->3)-α-D-galactopyranosyl-(1->4)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Efficient synthesis of globoside and isogloboside tetrasaccharides by using β(1→3) N-acetylgalactosaminyltransferase/UDP-N-acetylglucosamine C4 epimerase fusion protein

  摘要：

  构建了β(1→3)N-乙酰半乳糖胺基转移酶/UDP-N-乙酰葡萄糖胺C4差向异构酶融合蛋白，并将其用于耦合酶促反应，以相应的乳糖苷受体为原料合成了多种四糖和异四糖衍生物。

  DOI：

  10.1039/b300831b
• 作为产物：
  描述：

  uridine-5'-phosphoimidazolide 在 无机焦磷酸酶 、 uridine-5'-diphosphoglucose pyrophosphorylase 、 sodium perchlorate 、 三丁基焦磷酸铵 作用下， 生成 尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖
  参考文献：
  名称：

  Convenient syntheses of cytidine 5'-triphosphate, guanosine 5'-triphosphate, and uridine 5'-triphosphate and their use in the preparation of UDP-glucose, UDP-glucuronic acid, and GDP-mannose

  摘要：

  DOI：

  10.1021/jo00293a030
• 作为试剂：
  描述：

  尿苷-5'-三磷酸 、 半乳糖-1-磷酸 在 尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 无机焦磷酸酶 、 galactose-1-phosphate uridylyltransferase 、 glucose-1-phosphate uridylyltransferase 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 尿苷 5’-二二氧磷基半乳糖二钠盐
  参考文献：
  名称：

  Enzymatic synthesis of nucleobase-modified UDP-sugars: scope and limitations

  摘要：

  Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 400-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4 ''-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2014.12.005

文献信息

• The Novel UDP Glycosyltransferase 3A2: Cloning, Catalytic Properties, and Tissue Distribution
  作者：Peter I. MacKenzie、Anne Rogers、David J. Elliot、Nuy Chau、Julie-Ann Hulin、John O. Miners、Robyn Meech

  DOI：10.1124/mol.110.069336

  日期：2011.3

  The human UDP glycosyltransferase (UGT) 3A family is one of three families involved in the metabolism of small lipophilic compounds. Members of these families catalyze the addition of sugar residues to chemicals, which enhances their excretion from the body. The UGT1 and UGT2 family members primarily use UDP glucuronic acid to glucuronidate numerous compounds, such as steroids, bile acids, and therapeutic drugs. We showed recently that UGT3A1, the first member of the UGT3 family to be characterized, is unusual in using UDP N -acetylglucosamine as sugar donor, rather than UDP glucuronic acid or other UDP sugar nucleotides ( J Biol Chem 283: 36205–36210, 2008). Here, we report the cloning, expression, and characterization of UGT3A2, the second member of the UGT3 family. Like UGT3A1, UGT3A2 is inactive with UDP glucuronic acid as sugar donor. However, in contrast to UGT3A1, UGT3A2 uses both UDP glucose and UDP xylose but not UDP N -acetylglucosamine to glycosidate a broad range of substrates including 4-methylumbelliferone, 1-hydroxypyrene, bioflavones, and estrogens. It has low activity toward bile acids and androgens. UGT3A2 transcripts are found in the thymus, testis, and kidney but are barely detectable in the liver and gastrointestinal tract. The low expression of UGT3A2 in the latter, which are the main organs of drug metabolism, suggests that UGT3A2 has a more selective role in protecting the organs in which it is expressed against toxic insult rather than a more generalized role in drug metabolism. The broad substrate and novel UDP sugar specificity of UGT3A2 would be advantageous for such a function.

  人UDP-葡萄糖基转移酶(UGT)3A家族是涉及小脂溶性化合物代谢的三个家族之一。这些家族的成员催化糖残基添加到化学物质上,从而增强它们的排泄。UGT1和UGT2家族成员主要使用UDP-葡萄糖醛酸来糖苷化许多化合物,如类固醇、胆汁酸和治疗药物。我们最近表明,UGT3A1是第一个被表征的UGT3家族成员,它使用UDP N-乙酰葡萄糖胺作为糖供体,而不是UDP-葡萄糖醛酸或其他UDP糖核苷酸(J Biol Chem 283: 36205-36210, 2008)。在这里,我们报告了UGT3A2的克隆、表达和表征,UGT3A2是UGT3家族的第二个成员。与UGT3A1一样,UGT3A2在使用UDP-葡萄糖醛酸作为糖供体时无活性。然而,与UGT3A1不同,UGT3A2使用UDP葡萄糖和UDP木糖,但不使用UDP N-乙酰葡萄糖胺来糖苷化包括4-甲基伞形酮、1-羟基芘、生物类黄酮和雌激素在内的广泛底物。它对胆汁酸和雄激素的活性较低。UGT3A2的转录本存在于胸腺、睾丸和肾脏中,但在肝脏和胃肠道中几乎检测不到。UGT3A2在后者的主要器官中低表达,表明UGT3A2在这些器官中发挥选择性保护作用,抵御毒性损害,而不是在药物代谢中发挥更普遍的作用。UGT3A2广泛的底物和新颖的UDP糖特异性将有利于这种功能。
• Donor substrate promiscuity of bacterial β1–3-N-acetylglucosaminyltransferases and acceptor substrate flexibility of β1–4-galactosyltransferases
  作者：Yanhong Li、Mengyang Xue、Xue Sheng、Hai Yu、Jie Zeng、Vireak Thon、Yi Chen、Musleh M. Muthana、Peng G. Wang、Xi Chen

  DOI：10.1016/j.bmc.2016.02.043

  日期：2016.4

  beta4GalTs, donor substrate specificity studies of two bacterial beta3GlcNAcTs from Helicobacter pylori (Hpbeta3GlcNAcT) and Neisseria meningitidis (NmLgtA), respectively, using a library of 39 sugar nucleotides were carried out. The two beta3GlcNAcTs have complementary donor substrate promiscuity and 13 different trisaccharides were produced. They were used to investigate the acceptor substrate specificities

  beta1-3-N-乙酰氨基葡萄糖氨基转移酶（beta3GlcNAcTs）和beta1-4-半乳糖基转移酶（beta4GalTs）已广泛用于酶法合成含N-乙酰乳糖胺（LacNAc）的寡糖和包括聚LacNAc和乳糖（N-新四糖）的糖缀合物LNnT）存在于人类和其他哺乳动物的乳汁中。为了探索可以通过β3GlcNAcT和β4GalT的组合合成的寡糖和衍生物，分别使用39个糖核苷酸库对来自幽门螺杆菌（Hpbeta3GlcNAcT）和脑膜炎奈瑟氏球菌（NmLgtA）的两种细菌β3GlcNAcT的供体底物特异性进行了研究。执行。这两个beta3GlcNAcT具有互补的供体底物混杂，并产生了13种不同的三糖。他们分别用来研究三种脑膜炎奈瑟氏球菌（NmLgtB），幽门螺杆菌（Hpbeta4GalT）和牛（Bbeta4GalT）的beta4GalT的受体底物特异性。13种三糖中有10种被证明是这些beta4
• Synthesis of Galactose-Terminated Oligosaccharides by Use of Galactosyltransferase
  作者：Joachim Thiem、Torsten Wiemann

  DOI：10.1055/s-1992-34174

  日期：——

  Galactosyltransferase catalyzes the galactosylation of oligosaccharides terminated by glucose and by 2-acetamido-2-deoxy glucopyranose, respectively. Variations concerning the acceptor substrate as well as the donor substrate are described.

  半乳糖基转移酶分别催化以葡萄糖和2-乙酰胺基-2-脱氧吡喃葡萄糖为末端的多糖的半乳糖基化反应。本文描述了关于受体底物和供体底物的变化。
• Efficient one-pot multienzyme synthesis of UDP-sugars using a promiscuous UDP-sugar pyrophosphorylase from Bifidobacterium longum (BLUSP)
  作者：Musleh M. Muthana、Jingyao Qu、Yanhong Li、Lei Zhang、Hai Yu、Li Ding、Hamed Malekan、Xi Chen

  DOI：10.1039/c2cc17577k

  日期：——

  A promiscuous UDP-sugar pyrophosphorylase (BLUSP) was cloned from Bifidobacterium longum strain ATCC55813 and used efficiently with a Pasteurella multocida inorganic pyrophosphatase (PmPpA) with or without a monosaccharide 1-kinase for one-pot multienzyme synthesis of UDP-galactose, UDP-glucose, UDP-mannose, and their derivatives. Further chemical diversification of a UDP-mannose derivative resulted in the formation of UDP-N-acetylmannosamine.

  从双歧杆菌（Bifidobacterium longum）ATCC55813株中克隆得到一种非特异的UDP-糖焦磷酸化酶（BLUSP），并将其与巴氏杆菌（Pasteurella multocida）的无机焦磷酸酶（PmPpA）有效配合使用，无论是否加入单糖1-激酶，都能实现UDP-半乳糖、UDP-葡萄糖、UDP-甘露糖及其衍生物的一锅法多酶合成。进一步对UDP-甘露糖衍生物进行化学修饰，形成了UDP-N-乙酰甘露糖胺。
• CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20140235575A1

  公开（公告）日：2014-08-21

  The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

  本发明提供了一种一锅多酶法，用于从简单糖起始材料制备UDP糖。该发明还提供了一种一锅多酶法，用于从简单糖起始材料制备寡糖。