uridine 5'-phosphorothioate | 15548-52-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: uridine 5'-phosphorothioate
• 英文别名: uridine-5’-O-monophosphorothioate；O-((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl)methyl O,O-dihydrogen phosphorothioate；5’-UMPS；Uridin-5'-phosphorthionsaeure；[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-sulfanylphosphinic acid
• CAS: 15548-52-4
• 化学式: C₉H₁₃N₂O₈PS
• 分子量: 340.251
• InChiKey: NSEBKRRODBXALJ-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  uridine 5'-phosphorothioate 在 水 作用下， 生成 尿嘧啶核苷 、 尿苷5-单磷酸
  参考文献：
  名称：

  Hydrolytic dethiophosphorylation and desulfurization of the monothioate analogues of uridine monophosphates under acidic conditions

  摘要：

  The hydrolytic reactions of uridine 2'-, 3'- and 5'-phosphoromonothioates (2'-, 3'- and 5'-UMPS) under acidic and neutral conditions have been followed by HPLC. Under slightly acidic conditions (pH 2-5), only pa-independent dethiophosphorylation to uridine takes place. This reaction is 200- to 300-fold as fast as dephosphorylation of the corresponding uridine monophosphates (UMP), presumably due to higher stability of the thiometaphosphate monoanion compared to metaphosphate anion. At pH > 5, i.e. at pH > pK(a2) of the thiophosphate moiety, the dethiophosphorylation is retarded with increasing basicity of the solution. At pH < 1, acid-catalysed desulfurization of 2'- and 3'-UMPS to an isomeric mixture of 2'/3'-UMP competes with their dethiophosphorylation. This reaction is suggested to proceed by a nucleophilic attack of the neighbouring hydroxy group on phosphorus. No such reaction occurs with 5'-UMPS. In contrast to 2'- and 3'-UMP, no sign of interconversion of 2'- and 3'-UMPS is detected.

  DOI：

  10.1039/p29960000771
• 作为产物：
  描述：

  尿嘧啶核苷 在 2,6-二甲基吡啶 、 三氯硫磷 、 奎宁 、 水 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到uridine 5'-phosphorothioate
  参考文献：
  名称：

  金鸡纳生物碱催化的新机制允许有效的硫代磷酸化反应

  摘要：

  使用金鸡纳生物碱催化剂，在温和的反应条件下，使用市售的硫代磷酰氯高效合成核苷 5'-单硫代磷酸酯。对该反应进行了详细的机理研究，结合了反应动力学、核磁共振光谱和计算模型，以更好地了解观察到的反应性。总的来说，结果支持此类有机催化剂的前所未有的机制。

  DOI：

  10.1021/jacs.0c09192

文献信息

• Kinetic studies and predictions on the hydrolysis and aminolysis of esters of 2-<i>S</i>-phosphorylacetates
  作者：Milena Trmčić、David R W Hodgson

  DOI：10.3762/bjoc.6.87

  日期：——

  and aminolysis in comparison to their simple acetate progenitors, but their calculated selectivity towards aminolysis vs hydrolysis, while reasonable, would not lead to clean reactions that do not require purification. Extrapolations of the kinetic data were used to predict leaving group pK(a) values that could lead to improved selectivity towards aminolysis while retaining reasonable reaction times

  背景：异双功能交联剂可用于蛋白质科学和有机合成。水性体系中反应性酯的氨解通常用于生物共轭化学，但它必须与水解过程竞争。在这里，我们研究了 2-S-磷酸乙酸酯中间体的氨解和水解动力学，这些中间体是由常用的溴乙酸酯交联剂中的硫代磷酸酯亲核试剂取代溴化物引起的。结果：我们发现使用 N-羟基苯并三唑和 N-羟基琥珀酰亚胺溴乙酸盐在尿苷-5'-单硫代磷酸酯和 D-氨基葡萄糖之间的交联是无效的。为了深入了解这些不足，2-S-(5' -硫代磷酰尿苷）乙酸酯是使用溴乙酸对硝基苯酯或溴乙酸间硝基苯酯与尿苷-5'-单硫代磷酸酯组合制备的。所得对和间硝基苯基 2-S-(5'-硫代磷酰尿苷) 乙酸酯的水解和氨解动力学通过分光光度法监测酚盐离子的形成作为 pH 的函数来确定。尽管其硝基苯酚离去基团的 pK(aH) 值存在显着差异，但对和间硝基苯基 2-S-(5'-硫代磷酰尿苷) 乙酸酯显示出相似的反应性曲线。与它们
• Hydrolytic (in)stability of phosphate isosteres
  作者：Molhm Nassir、Avinoam Isaak、Bilha Fischer

  DOI：10.1016/j.ejmech.2022.114836

  日期：2022.12

  life, was studied extensively along with the chemical hydrolytic reaction. The metabolic instability of nucleotides, in contrast with their enormous chemical stability, triggered development of metabolically stable phosphate isosteres. However, their chemical stability has not been reported. Here, we fill this gap by exploring the hydrolytic stability of the thiophosphate (PS) and dithiophosphate (PS2)

  几十年来，作为生命基石的核苷酸的酶水解与化学水解反应一起得到了广泛研究。与其巨大的化学稳定性相反，核苷酸的代谢不稳定性引发了代谢稳定的磷酸盐电子等排体的发展。然而，尚未报道它们的化学稳定性。在这里，我们通过探索硫代磷酸盐 (PS) 和二硫代磷酸盐 (PS 2 ) 单酯等排物家族的水解稳定性来填补这一空白。尿苷-PS 和 -PS 2（UMPS 和 UMPS 2 ）的动力学实验可以绘制出它们的稳定性边界。此外，表征 UMPS 和 UMPS 2的几个化学和结构特征提供见解，这解释了核苷酸磷酸链不同位置的PS 或 PS 2部分的显着不同稳定性。我们的结论可能会指导应用磷酸盐电子等排物并允许选择最佳电子等排物的广泛科学界。
• Methods for modulating taste receptors
  申请人：MARS, INCORPORATED

  公开号：US11185100B2

  公开（公告）日：2021-11-30

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.

  本文描述了存在于鲜味受体结构域中的氨基酸，其中氨基酸与至少一种核苷酸衍生物和/或至少一种跨膜化合物相互作用，从而增强、调节、增加和/或提高鲜味受体的活性。此类化合物可用于调味组合物，以增强食品的鲜味和/或适口性。
• Immobilized poly(n)polymerase
  申请人：CureVac AG

  公开号：US11384375B2

  公开（公告）日：2022-07-12

  The present invention relates to an immobilized poly(N)polymerase (PNP), methods of producing said PNP and uses thereof. Further disclosed is an enzyme reactor and kit comprising the PNP for producing polynucleotidylated ribonucleic acid poly(N)RNA)molecules which are useful in gene therapy, immunotherapy, protein replacement therapy and/or vaccination.

  本发明涉及一种固定化聚(N)聚合酶(PNP)、生产所述 PNP 的方法及其用途。本发明还公开了一种酶反应器和包含 PNP 的试剂盒，用于生产基因治疗、免疫治疗、蛋白质替代疗法和/或疫苗接种中有用的多核苷酸化核糖核酸 poly(N)RNA) 分子。
• Post-synthesis labeling of nucleic acids, assays using nucleic acids that are labeled post-synthetically, single nucleotide polymorphism detection, and associated compounds and microarrays
  申请人：MOTOROLA, INC.

  公开号：US20030119005A1

  公开（公告）日：2003-06-26

  An assay is provided for nucleic acids that can be post-synthetically labeled, wherein modified nucleoside triphosphates are used that are more efficiently and specifically incorporated during nucleic acid synthesis than labeled nucleoside triphosphates. In a preferred embodiment, nucleoside &agr;-thiotriphosphates are utilized. Maleimide or iodoacetamide conjugating moieties can be attached post-synthetically. The conjugating moieties may include a reporter group. Also disclosed are new methods for detecting single nucleotide polymorphism.

  提供了一种可在合成后标记核酸的检测方法，其中使用了修饰的核苷三磷酸酯，这种核苷三磷酸酯在核酸合成过程中比标记的核苷三磷酸酯更有效、更特异。在一个优选的实施方案中，使用的是核苷三磷酸酯。马来酰亚胺或碘乙酰胺共轭分子可在合成后连接。共轭分子可包括报告基团。还公开了检测单核苷酸多态性的新方法。