thymidine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate) | 289902-34-7

• 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: thymidine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate)
• 英文别名: TDP-D-olivose；TDP-α-D-2-deoxyglucose；dTDP-2-deoxy-D-Glc；deoxy-thymidine-diphosphate-2-deoxyglucose；TDP-2-deoxyglucose；[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] hydrogen phosphate
• CAS: 289902-34-7
• 化学式: C₁₆H₂₆N₂O₁₅P₂
• 分子量: 548.334
• InChiKey: IWMJODNYWRQXAG-AOUWHDERSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  251
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  thymidine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate) 、 3,4-二氯苯酚 在 glycosyltransferases YdhE bacillus licheniformi 、 magnesium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  两种三官能的卢卢尔糖基转移酶作为天然产物糖多样化的生物催化剂。

  摘要：

  两种混杂的地衣芽孢杆菌糖基转移酶YdhE和YojK表现出20种不同类别的59种结构不同的天然和非天然产物的突出的立体特异性但非区域特异性的糖基化活性。两种酶都在各种化合物的三个亲核基团（OH，NH 2，SH）上转移了各种糖，从而生成O-，N-和S-糖苷。这些酶还显示了一锅转糖基化的催化可逆性潜力，因此在药物发现中赋予了糖多样化天然产物生物合成的经济有效应用。

  DOI：

  10.1021/acs.orglett.9b03040
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-benzoyl-2-deoxy-1-thio-β-D-glucopyranoside 在 palladium on activated charcoal 、 galactose-1-phosphate thymidylyltransferase sodium hydroxide 、 N-Iodosuccinamide 、 三氟甲磺酸 、 magnesium 、 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 thymidine 5'-(2-deoxy-α-D-glucopyranosyl diphosphate)
  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。
• 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。
• Systematic Enzymatic Synthesis of dTDP‐Activated Sugar Nucleotides
  作者：Fangyu Wei、Rui Yuan、Qin Wen、Liuqing Wen

  DOI：10.1002/anie.202217894

  日期：——

  On the basis of the de novo and salvage biosynthetic pathways, diverse dTDP-activated sugar nucleotides, which are important but difficult to access, were successfully prepared on a large scale from readily available starting materials. This high-yielding synthetic strategy avoids the need for complicated purification procedures.

  在从头和补救生物合成途径的基础上，从容易获得的起始材料成功地大规模制备了多种重要但难以获得的 dTDP 活化糖核苷酸。这种高产合成策略避免了复杂的纯化程序。
• Glycorandomization and the production of novel erythronolide and coumarin analogs
  申请人：——

  公开号：US20030068669A1

  公开（公告）日：2003-04-10

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。
• Glycorandomization and production of novel vancomycin analogs
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20040259228A1

  公开（公告）日：2004-12-23

  The present invention provides combinatorial methods for rapidly generating a diverse library of glycorandomized structures, comprising incubating one or more aglycons and a pool of NDP-sugars in the presence of a glycosyltransferase. The glycosyltransferase may be one that is associated with or involved in production of natural secondary metabolites, or one which is putatively associated with or involved in production of natural secondary metabolites. The glycosyltransferase may show significant flexibility with respect to its NDP-sugar donors and/or its aglycons. NDP-sugar donors may be commercially available, or may be produced by utilizing mutant or wild type nucleotidyltransferases significant flexibility with respect to their substrates.

  本发明提供了快速生成多种糖随机化结构库的组合方法，包括在糖基转移酶存在下培养一种或多种琼脂糖和NDP-糖池。糖基转移酶可以是与天然次生代谢物的生产有关或参与生产的糖基转移酶，也可以是推测与天然次生代谢物的生产有关或参与生产的糖基转移酶。糖基转移酶在其 NDP-糖供体和/或其糖醛酸方面可以表现出很大的灵活性。NDP 糖供体可以从市场上买到，也可以通过利用突变型或野生型核苷酸转移酶对底物的极大灵活性来生产。