α-D-glucose-1-phosphate | 76939-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucose-1-phosphate
• 英文别名: glucose-1-phosphate；alpha-D-Glucopyranose 1-phosphate；[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
• CAS: 76939-53-2
• 化学式: C₆H₁₁O₉P
• 分子量: 258.122
• InChiKey: HXXFSFRBOHSIMQ-VFUOTHLCSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  163
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  α-D-glucose-1-phosphate 生成 D-glucose 6-phosphate
  参考文献：
  名称：

  Among Multiple Phosphomannomutase Gene Orthologues, Only One Gene Encodes a Protein with Phosphoglucomutase and Phosphomannomutase Activities in Thermococcus kodakaraensis

  摘要：

  摘要 在嗜热古生菌Thermococcus kodakaraensis的基因组中发现了四个可被注释为磷甘露糖酶（PMM）基因（COG1109）的同源基因（TK1108、TK1404、TK1777和TK2185）。 热球菌 KOD1。我们之前发现 TK1777 实际上编码一种磷酸戊二酸酶。为了确定其余三个直向同源物中哪个编码磷酸葡聚糖突变酶（PGM），我们研究了 T. kodakaraensis KOD1 的 PGM 活性。 细胞中的 PGM 活性。 细胞中的 PGM 活性，并确定了负责这种活性的基因。异源基因表达以及重组蛋白的纯化和表征表明，TK1108编码的蛋白具有高水平的PGM活性（690 U mg -1 ）以及高水平 PMM 活性（401 U mg -1 ).对其余两个直向同源物的类似分析表明，它们的蛋白产物既不表现出 PGM 活性，也不表现出 PMM 活性。T. kodakaraensis 中 TK1108 的 PGM 活性和转录 T. kodakaraensis 的 PGM 活性和转录均高于以淀粉为原料的细胞。我们的研究结果清楚地表明，在柯达卡拉氏菌的四个 PMM 基因直向同源物中 中，只有一个基因 中，只有一个基因 TK1108 实际编码具有 PGM 和 PMM 活性的蛋白质。

  DOI：

  10.1128/jb.186.18.6070-6076.2004
• 作为产物：
  描述：

  laminaribiose 在 ACL₀₇₂₉ 、 hydrogenphosphate 、 sodium hydroxide 、 4-羟乙基哌嗪乙磺酸 作用下， 以 水 为溶剂， 生成 D-葡萄糖 、 α-D-glucose-1-phosphate
  参考文献：
  名称：

  Characterization of a laminaribiose phosphorylase from Acholeplasma laidlawii PG-8A and production of 1,3-β-d-glucosyl disaccharides

  摘要：

  We identified a glycoside hydrolase family 94 homolog (ACL0729) from Acholeplasma laidlawii PG-8A as a laminaribiose (1,3-beta-D-glucobiose) phosphorylase (EC 2.4.1.31). The recombinant ACL0729 produced in Escherichia coli catalyzed phosphorolysis of laminaribiose with inversion of the anomeric configuration in a typical sequential bi bi mechanism releasing alpha-D-glucose 1-phosphate and D-glucose. Laminaritriose (1,3-beta-D-glucotriose) was not an efficient substrate for ACL0729. The phosphorolysis is reversible, enabling synthesis of 1,3-beta-D-glucosyl disaccharides by reverse phosphorolysis with strict regioselectivity from alpha-D-glucose 1-phosphate as the donor and suitable monosaccharide acceptors (D-glucose, 2-deoxy-D-arabino-hexopyranose, D-xylose, D-glucuronic acid, 1,5-anhydro-D-glucitol, and D-mannose) with C-3 and C-4 equatorial hydroxyl groups. The D-glucose and 2-deoxy-D-arabino-hexopyranose caused significantly strong competitive substrate inhibition compared with other glucobiose phosphorylases reported, in which the acceptor competitively inhibited the binding of the donor substrate. By contrast, none of the examined disaccharides served as acceptor in the synthetic reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.006

文献信息

• <i>In situ</i>proton NMR study of acetyl and formyl group migration in mono-<i>O</i>-acyl D-glucose
  作者：Lothar Brecker、Marek Mahut、Alexandra Schwarz、Bernd Nidetzky

  DOI：10.1002/mrc.2395

  日期：2009.4

  Acetyl and formyl group migration, mutarotation, and hydrolysis of mono-O-acylated glucose are studied by in situ 1D and 2D (1)H NMR spectroscopy. Alpha-D-glucosyl-1-acetate and alpha-D-glucosyl-1-formate serve as sole starting materials. They are generated in situ by configuration retaining glucosyltransfer from alpha-D-glucosyl-1-phosphate to formate and acetate, which is catalyzed by the Glu-237

  通过原位1D和2D（1）H NMR光谱研究了单O酰化葡萄糖的乙酰基和甲酰基迁移，诱变和水解。α-D-葡萄糖基-1-乙酸酯和α-D-葡萄糖基-1-甲酸酯是唯一的起始原料。它们是通过保留从α-D-D-葡糖基-1-磷酸到甲酸和乙酸盐的葡糖基转移的构型而原位生成的，而这种转移是由肠膜肠隐球菌蔗糖磷酸化酶的Glu-237-> Gln突变体催化的。直接从反应混合物中鉴定，表征和定量临时累积的区域异构的单-O-酰基D-葡萄糖。转化的时程使人们了解了酰基迁移和诱变的pH依赖性以及各种区域异构体的稳定性。
• Identification and characterization of a strict and a promiscuous <i>N</i>-acetylglucosamine-1-P uridylyltransferase in <i>Arabidopsis</i>
  作者：Ting Yang、Merritt Echols、Andy Martin、Maor Bar-Peled

  DOI：10.1042/bj20100315

  日期：2010.9.1

  the UT family cause different substrate specificities. A three-dimensional protein structure model using the human AGX1 as template showed a conserved catalytic fold and helped identify key conserved motifs, despite the high sequence divergence. The identification of these strict and promiscuous gene products open a window to identify new roles of amino sugar metabolism in plants and specifically their

  UDP-GlcNAc是糖蛋白和糖脂合成的重要前体。在本研究中，鉴定了来自拟南芥的编码58.3 kDa GlcNAc1pUT-1（N-乙酰氨基葡萄糖-1-磷酸尿嘧啶转移酶）的功能性核苷酸转移酶基因。在正向反应中，酶催化由相应的单糖1-磷酸酯和UTP形成UDP-N-乙酰氨基葡萄糖和PPi。该酶也可以利用4-表位UDP-GalNAc作为底物。该酶需要二价离子（Mg2 +或Mn2 +）才能发挥活性，并且在pH 6.5和8.0之间以及30-37摄氏度下具有很高的活性。正向反应的表观Km值为337 microM（GlcNAc-1-P）和295。 microM（UTP）。发现与GlcNAc1pUT-1具有86％氨基酸序列同一性的另一个GlcNAc1pUT-2可以转化，除了GlcNAc-1-P和GalNAc-1-P之外，Glc-1-P进入相应的UDP糖中，表明UT家族的细微变化会导致不同的底物特异性。尽管
• 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。
• Identification of a novel UDP-sugar pyrophosphorylase with a broad substrate specificity in <i>Trypanosoma cruzi</i>
  作者：Ting Yang、Maor Bar-Peled

  DOI：10.1042/bj20100238

  日期：2010.8.1

  The diverse types of glycoconjugates synthesized by trypanosomatid parasites are unique compared with the host cells. These glycans are required for the parasite survival, invasion or evasion of the host immune system. Synthesis of those glycoconjugates requires a constant supply of nucleotide-sugars (NDP-sugars), yet little is known about how these NDP-sugars are made and supplied. In the present paper, we report a functional gene from Trypanosoma cruzi that encodes a nucleotidyltransferase, which is capable of transforming different types of sugar 1-phosphates and NTP into NDP-sugars. In the forward reaction, the enzyme catalyses the formation of UDP-glucose, UDP-galactose, UDP-xylose and UDP-glucuronic acid, from their respective monosaccharide 1-phosphates in the presence of UTP. The enzyme could also convert glucose 1-phosphate and TTP into TDP-glucose, albeit at lower efficiency. The enzyme requires bivalent ions (Mg2+ or Mn2+) for its activity and is highly active between pH 6.5 and pH 8.0, and at 30–42 °C. The apparent Km values for the forward reaction were 177 μM (glucose 1-phosphate) and 28.4 μM (UTP) respectively. The identification of this unusual parasite enzyme with such broad substrate specificities suggests an alternative pathway that might play an essential role for nucleotide-sugar biosynthesis and for the regulation of the NDP-sugar pool in the parasite.

  与宿主细胞相比，锥虫寄生虫合成的各种类型的聚糖是独一无二的。这些聚糖是寄生虫生存、入侵或躲避宿主免疫系统所必需的。合成这些聚糖需要核苷酸-糖（NDP-糖）的持续供应，但人们对这些 NDP-糖是如何制造和供应的知之甚少。本文报告了克氏锥虫的一个功能基因，该基因编码一种核苷酸转移酶，能够将不同类型的 1-磷酸和 NTP 糖转化为 NDP 糖。在正向反应中，该酶催化 UDP-葡萄糖、UDP-半乳糖、UDP-木糖和 UDP-葡萄糖醛酸在UTP 的存在下从各自的单糖 1-磷酸酯中生成 UDP-葡萄糖、UDP-半乳糖、UDP-木糖和 UDP-葡萄糖醛酸。该酶还能将 1-磷酸葡萄糖和 TTP 转化为 TDP-葡萄糖，但转化效率较低。该酶的活性需要二价离子（Mg2+ 或 Mn2+），在 pH 6.5 至 pH 8.0 之间和 30-42 ℃ 时活性很高。正向反应的表观 Km 值分别为 177 μM（1-磷酸葡萄糖）和 28.4 μM（UTP）。这种不寻常的寄生虫酶具有如此广泛的底物特异性，它的发现提示了一种可能在核苷酸-糖生物合成和调节寄生虫体内 NDP-糖库方面发挥重要作用的替代途径。
• HIGH-PERFORMANCE LIQUID CHROMATOGRAPHIC CHARACTERIZATION OF THE ROLE OF INORGANIC PYROPHOSPHATASE IN REGULATING THE REACTION OF URIDINE 5′-TRIPHOSPHATE WITH GLUCOSE 1-MONOPHOSPHATE
  作者：Hisanobu Hirano、Yoshinobu Baba、Norimasa Yoza、Shigeru Ohashi

  DOI：10.1246/cl.1986.633

  日期：1986.4.5

  Inorganic pyrophosphatase ( EC 3.6.1.1 ) catalyzing the hyrolysis of inorganic pyrophosphate drived the reaction of uridine 5′-triphosphate with glucose 1-monophosphate in the direction of uridine 5′-diphosphoglucose formation. The kinetic data in vitro supported the concept that inorganic pyrophosphate might be involved as one of products and its concentration level might regulate the above reaction in metabolic process.

  无机焦磷酸酶（EC 3.6.1.1）催化无机焦磷酸的热解，推动尿苷-5′-三磷酸与葡萄糖-1-单磷酸的反应，从而形成尿苷-5′-二磷酸葡萄糖。体外动力学数据支持了无机焦磷酸可能作为产物之一参与其中，其浓度水平可能会调节代谢过程中的上述反应的概念。