[5-(4-氨基-2-氧代-1(2H)-嘧啶基)-3,4-二羟基四氢-2-呋喃基]甲基3,4,5-三羟基-6-(羟基甲基)四氢-2H-吡喃-2-基二氢二磷酸酯 | 2906-23-2

• 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: [5-(4-氨基-2-氧代-1(2H)-嘧啶基)-3,4-二羟基四氢-2-呋喃基]甲基3,4,5-三羟基-6-(羟基甲基)四氢-2H-吡喃-2-基二氢二磷酸酯
• 英文名称: CDP-glucose
• 英文别名: CDP-D-glucose；cytidylyldiphosphate-α-D-glucose；cytidine-5'-(α-D-glucopyranosyl)diphosphate；Cytidindiphosphatglucose；O^5'-(2-α-L-glucopyranosyloxy-1,2-dihydroxy-diphosphoryl)-cytidine；cytidine-5'-diphospho-α-D-glucose；CDP-Glc；[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-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: 2906-23-2
• 化学式: C₁₅H₂₅N₃O₁₆P₂
• 分子量: 565.322
• InChiKey: CGPHZDRCVSLMCF-JZMIEXBBSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 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：
  301
• 氢给体数：
  9
• 氢受体数：
  16

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  胞苷-5’-二磷酸	cytidine diphosphate	63-38-7	C9H15N3O11P2	403.179
  胞苷-5’-三磷酸	cytidine triphosphate	65-47-4	C9H16N3O14P3	483.159

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	cytidylyldiphosphate-D-paratose	127179-55-9	C15H25N3O14P2	533.323
  ——	CDP-6-deoxy-D-glycero-L-threo-4-hexulose	6998-71-6	C15H23N3O15P2	547.306
  [(2R,3R,4R,5R)-5-(4-氨基-2-氧代-嘧啶-1-基)-3,4-二羟基-四氢呋喃-2-基]甲氧基-[羟基-[(2R,3R,6R)-3-羟基-6-甲基-5-氧代-四氢吡喃-2-基]氧基-磷酰]氧基-次磷酸	cytidylyldiphosphate-3,6-dideoxy-D-glycero-4-hexulose	21870-27-9	C15H23N3O14P2	531.307

反应信息

• 作为反应物：
  描述：

  [5-(4-氨基-2-氧代-1(2H)-嘧啶基)-3,4-二羟基四氢-2-呋喃基]甲基3,4,5-三羟基-6-(羟基甲基)四氢-2H-吡喃-2-基二氢二磷酸酯 在 <4S-2H>NADPH 、 CDP-D-glucose 4,6-dehydratase 、 paratose synthase 、 三羟甲基氨基甲烷盐酸盐 作用下， 以 水 为溶剂， 反应 2.0h， 生成 CDP-6-deoxy-D-<4-2H>glucose
  参考文献：
  名称：

  氢化物转移对CDP-d-葡萄糖4,6-脱水酶中催化循环NAD +的立体特异性

  摘要：

  在3,6-脱氧糖的生物合成途径中发现的CDP-D-葡萄糖4,6-脱水酶（E od）含有紧密结合的NAD +，可在催化过程中循环使用。通过分析脱辅酶与立体特异性标记的NADH及其产物CDP-6-脱氧-D-甘油一起孵育时产生的NAD +，可以确定氢化物在E od中与辅酶之间的转移的立体化学偏好为pro-S。-L-苏式-4-己糖。

  DOI：

  10.1016/s0040-4020(98)01005-9
• 作为产物：
  描述：

  胞苷-5’-三磷酸 、 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87%的产率得到[5-(4-氨基-2-氧代-1(2H)-嘧啶基)-3,4-二羟基四氢-2-呋喃基]甲基3,4,5-三羟基-6-(羟基甲基)四氢-2H-吡喃-2-基二氢二磷酸酯
  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

• New Insights into the Mechanism of CDP-<scp>d</scp>-Tyvelose 2-Epimerase:  An Enzyme-Catalyzing Epimerization at an Unactivated Stereocenter
  作者：Tina M. Hallis、Zongbao Zhao、Hung-wen Liu

  DOI：10.1021/ja0022021

  日期：2000.11.1

  the well-studied UDP-d-galactose 4-epimerase, that can invert unactivated stereocenters. To study the mechanism of this enzyme, we have cloned and expressed the tyv gene that encodes CDP-d-tyvelose 2-epimerase. The purified tetrameric protein contains approximately one equivalent of bound NAD+ per monomer and a small fraction of NADH. Four possible mechanisms involving NAD+ can be proposed for this enzyme;

  Tyvelose 是一种 3,6-二脱氧己糖，存在于 Yersinia pseudotuberculosis IVA 的 O-抗原中，并且是此类糖中唯一一种直接由另一种 3,6-双脱氧己糖，paratose 产生的糖。这种转化所需的 C-2 差向异构化已被提议由 CDP-d-泰维糖 2-差向异构酶催化。这种酶很有趣，因为它属于一组差向异构酶，包括经过充分研究的 UDP-d-半乳糖 4-差向异构酶，可以反转未激活的立体中心。为了研究这种酶的作用机制，我们克隆并表达了编码 CDP-d-tyvelose 2-epimerase 的 tyv 基因。纯化的四聚体蛋白含有大约一当量的结合 NAD+ 每个单体和一小部分 NADH。对于这种酶，可以提出四种涉及 NAD+ 的可能机制；两个涉及底物 C-2 处的氧化，而另外两个需要在 C-4 处氧化。在之前的一篇文章中，我们提供了支持由 C-4 发起的复古醇醛型机制的初步数据
• 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.
• Wong, Chi-Huey; Ichikawa, Yoshitaka; Krach, Thomas, Journal of the American Chemical Society, 1991, vol. 113, # 21, p. 8137 - 8145
  作者：Wong, Chi-Huey、Ichikawa, Yoshitaka、Krach, Thomas、Narvor, Christine Gautheron-Le、Dumas, David P.、Look, Gary C.

  DOI：——

  日期：——
• Catalytic reversibility of Pyrococcus horikoshii trehalose synthase: Efficient synthesis of several nucleoside diphosphate glucoses with enzyme recycling
  作者：Soo-In Ryu、Jeong-Eun Kim、Eun-Joo Kim、Seung-Kyung Chung、Soo-Bok Lee

  DOI：10.1016/j.procbio.2010.07.030

  日期：2011.1

  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.