dTDP-α-D-mannose

• 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
• 英文名称: dTDP-α-D-mannose
• 英文别名: thymidine 5'-(α-D-mannopyranosyl diphosphate)；dTDP-D-Man；dTDP-Man；dTDP-mannose；[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] [(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• 化学式: C₁₆H₂₆N₂O₁₆P₂
• 分子量: 564.334
• InChiKey: YSYKRGRSMLTJNL-GVFWWPKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  mannose-1-phosphate 、 beta-胸苷 在 galactose-1-phosphate thymidylyltransferase magnesium 作用下， 反应 0.5h， 生成 dTDP-α-D-mannose
  参考文献：
  名称：

  合成天然和“非天然”UDP-和 TDP-核苷酸糖的通用酶法

  摘要：

  DOI：

  10.1021/ja001444y

文献信息

• Active-site engineering of nucleotidylyltransferases and general enzymatic methods for the synthesis of natural and "unnatural" UDP- and TDP-nucleotide sugars
  申请人：——

  公开号：US20030055235A1

  公开（公告）日：2003-03-20

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified Ep or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了一种突变型核苷酸转移酶，如E p ，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或修饰的Ep或其他核苷酸转移酶合成所需的核苷酸糖的方法；以及通过本发明方法合成的核苷酸糖。本发明进一步提供了新的糖基磷酸酯，及其制造方法。
• Synthesis of α-Deoxymono and Difluorohexopyranosyl 1-Phosphates and Kinetic Evaluation with Thymidylyl- and Guanidylyltransferases
  作者：Jian-She Zhu、Nicole E. McCormick、Shannon C. Timmons、David L. Jakeman

  DOI：10.1021/acs.joc.6b01485

  日期：2016.10.7

  monofluoro substitution at C-2, C-4, and C-6 and difluoro substitution at C-2 within two orders of magnitude. In contrast, the kinetic analysis of GDP-ManPP was only possible with three out of eight analogues. The pKa2 values of analogues (1–3) were determined by proton decoupled 31P and 19F NMR titration experiments. Counterintuitively, the axial fluoro substituent in 3 did not change chemical shift upon

  已经合成了八个氟化的等排α - d-吡喃葡萄糖基1-磷酸酯（Glc 1P）类似物。胸腺嘧啶转移酶Cps2L和胍基转移酶GDP-ManPP与这些类似物的滥交调查显示，除1,6-二磷酸6以外，所有这些均被任一酶所接受。使用连续偶联测定法确定这些类似物的动力学参数。这些数据证明了Cps2L的广泛底物滥交，k cat / K mC-2，C-4和C-6处的单氟取代和C-2处的二氟取代在两个数量级内变化。相反，只有八分之三的类似物才能对GDP-ManPP进行动力学分析。在p ķ一个2个类似物的值（1 - 3）通过质子去耦测定31 P和19个F NMR滴定实验。与直觉相反，在3中的轴向氟取代基在滴定时没有改变化学位移，并且与单氟类似物相比，二氟类似物的酸度没有显着增加。在所有五种底物之间均未观察到强烈的布朗斯台德线性自由能相关性（1 –3，Glc 1P和Man 1P）用于任一酶催化的反应。但是，在选定的
• Exploring the broad nucleotide triphosphate and sugar-1-phosphate specificity of thymidylyltransferase Cps23FL from <i>Streptococcus pneumonia</i> serotype 23F
  作者：Siqiang Li、Hong Wang、Guoxia Jin、Zonggang Chen、Guofeng Gu

  DOI：10.1039/d0ra05799a

  日期：——

  is the initial enzyme that catalyses the thymidylyl transfer reaction in prokaryotic deoxythymidine diphosphate-L-rhamnose (dTDP-Rha) biosynthetic pathway. In this study, the broad substrate specificity of Cps23FL towards six glucose-1-phosphates and nine nucleoside triphosphates as substrates was systematically explored, eventually providing access to nineteen sugar nucleotide analogs.

  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。
• 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。
• ACTIVE-SITE ENGINEERING OF NUCLEOTIDYLYLTRANSFERASES AND GENERAL ENZYMATIC METHODS FOR THE SYNTHESIS OF NATURAL AND "UNNATURAL" UDP- AND TDP-NUCLEOTIDE SUGARS
  申请人：THORSON Jon

  公开号：US20070178487A1

  公开（公告）日：2007-08-02

  The present invention provides mutant nucleotidylyl-transferases, such as E p , having altered substrate specificity; methods for their production; and methods of producing nucleotide sugars, which utilize these nucleotidylyl-transferases. The present invention also provides methods of synthesizing desired nucleotide sugars using natural and/or modified E p or other nucleotidyltransferases; and nucleotide sugars sythesized by the present methods. The present invention further provides new glycosyl phosphates, and methods for making them.

  本发明提供了突变核苷酸转移酶，例如Ep，具有改变的底物特异性；其生产方法；以及利用这些核苷酸转移酶生产核苷酸糖的方法。本发明还提供了使用天然和/或改性的Epor或其他核苷酸转移酶合成所需核苷酸糖的方法；以及通过本方法合成的核苷酸糖。本发明还提供了新的糖基磷酸酯，以及制备它们的方法。