Thymidine-5'-diphospho-beta-D-xylose

• 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'-diphospho-beta-D-xylose
• 英文别名: [hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] [(2R,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl] hydrogen phosphate
• 化学式: C₁₅H₂₄N₂O₁₅P₂
• 分子量: 534.307
• InChiKey: AJUADKZRQSBUAK-KDGZBOQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  novobiocic acid 、 Thymidine-5'-diphospho-beta-D-xylose 在 苯磺酰胺 、 NovM-His₆ 、 magnesium chloride 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 4-Hydroxy-N-[4-hydroxy-8-methyl-2-oxo-7-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-2H-chromen-3-yl]-3-(3-methyl-but-2-enyl)-benzamide
  参考文献：
  名称：

  Substrate Specificity of NovM:  Implications for Novobiocin Biosynthesis and Glycorandomization

  摘要：

  In an effort to expand the scope of natural product in vitro glycorandomization (IVG), the substrate specificity of NovM was investigated. A test of four aglycon analogues and over 40 nucleotide sugars revealed NovM has a surprisingly stringent substrate specificity and provided only three new "unnatural" natural products. On the basis of the determined substrate specificity, an alternative to the sugar nucleotide biosynthetic dogma and a cautionary note for the general applicability of IVG are introduced.

  DOI：

  10.1021/ol0341086
• 作为产物：
  描述：

  D-葡萄糖醛酸 、 胸苷-5'-三磷酸 在 pyrophosphatase 、 silver nitrate 、 D-GlcA kinase from Arabidopsis thaliana 、 dTDP-Glc pyrophosphorylase was from Salmonella enterica 、 UDP-Gal pyrophosphorylase from Pyrococcus furiosus 、 二磷酸腺苷 、 5’-三磷酸腺苷 、 sodium chloride 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 以62 %的产率得到Thymidine-5'-diphospho-beta-D-xylose
  参考文献：
  名称：

  dTDP 激活的糖核苷酸的系统酶促合成

  摘要：

  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。

  DOI：

  10.1002/anie.202217894

文献信息

• 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。
• GLYCORANDOMIZATION AND THE PRODUCTION OF NOVEL ERYTHRONOLIDE AND COUMARIN ANALOGS
  申请人：Thorson S. Jon

  公开号：US20050266523A1

  公开（公告）日：2005-12-01

  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：Thorson Jon

  公开号：US20080268504A1

  公开（公告）日：2008-10-30

  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.
• Glycorandomization and Production of Novel Novobiocin Analogs
  申请人：Thorson Jon

  公开号：US20120264924A1

  公开（公告）日：2012-10-18

  The present invention provides glycorandomized structures and 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.