uridine-5'-diphospho-2-deoxy-α-D-glucopyranose

• 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: uridine-5'-diphospho-2-deoxy-α-D-glucopyranose
• 英文别名: uridine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate)；uridine 5'-diphospho-2-deoxy-α-D-glucopyranoside；UDP-2-deoxyGlc；[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] hydrogen phosphate；[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• 化学式: C₁₅H₂₄N₂O₁₆P₂
• 分子量: 550.307
• InChiKey: MEJLHDUXDMCALH-GUBZJDGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 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

• 作为反应物：
  描述：

  uridine-5'-diphospho-2-deoxy-α-D-glucopyranose 生成 UDP-2-deoxy-Gal
  参考文献：
  名称：

  Synthesis of Galactose-Terminated Oligosaccharides by Use of Galactosyltransferase

  摘要：

  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。

  DOI：

  10.1055/s-1992-34174
• 作为产物：
  描述：

  2-Deoxy-D-glucose 在 尿苷-5'-三磷酸 作用下， 以 水 为溶剂， 反应 96.0h， 生成 uridine-5'-diphospho-2-deoxy-α-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Galactose-Terminated Oligosaccharides by Use of Galactosyltransferase

  摘要：

  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。

  DOI：

  10.1055/s-1992-34174

文献信息

• 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。
• 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。
• Isotope Probing of the UDP-Apiose/UDP-Xylose Synthase Reaction: Evidence of a Mechanism via a Coupled Oxidation and Aldol Cleavage
  作者：Thomas Eixelsberger、Doroteja Horvat、Alexander Gutmann、Hansjörg Weber、Bernd Nidetzky

  DOI：10.1002/anie.201609288

  日期：2017.2.20

  initiating step of pyranoside-to-furanoside conversion, did not give the corresponding Api product. Kinetic isotope effects (KIEs) support an UAXS mechanism in which substrate oxidation by enzyme-NAD+ and retro-aldol sugar ring-opening occur coupled in a single rate-limiting step leading to decarboxylation. Rearrangement and ring-contracting aldol addition in an open-chain intermediate then give the UDP-Api

  C分支糖d-apiose（Api）对植物细胞壁发育至关重要。酶催化的脱羧/吡喃糖苷环收缩反应从UDP-α-d-葡萄糖醛酸（UDP-GlcA）到Api前体UDP-α-d-apiose（UDP-Api）。我们检查了具有站点选择性2 H标记和脱氧底物的UDP-Api /UDP-α-d-木糖合酶（UAXS）的机制。防止C-2 / C-3羟醛裂解的类似的UDP-2-脱氧-GlcA类似物，可能是吡喃糖苷向呋喃糖苷转化的起始步骤，但未提供相应的Api产物。动力学同位素效应（KIE）支持UAXS机制，其中通过酶NAD +和逆醛醇糖开环发生的底物氧化发生在导致脱羧的单个限速步骤中。
• 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。