4-硫代-UDP | 24868-15-3

• 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
• 中文名称: 4-硫代-UDP
• 英文名称: 4-Thiouridin-5'-diphosphat
• 英文别名: 4-Thio-UDP；[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl phosphono hydrogen phosphate
• CAS: 24868-15-3
• 化学式: C₉H₁₄N₂O₁₁P₂S
• 分子量: 420.23
• InChiKey: OGVPOARJPKSLBM-XVFCMESISA-N

物化性质

• 密度：
  2.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  227
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-硫代-UDP 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2R,3R,4S,5R)-4-(1-(3,4-dihydroxy-5-(diphosphoryloxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylthio)-butanoic acid ammonium salt
  参考文献：
  名称：

  尿苷 5'-二磷酸类似物在人 P2Y6 受体上的结构-活性关系。

  摘要：

  研究了尿嘧啶核苷酸激活的 P2Y6 受体的结构-活性关系和分子模型。合成了带有核糖部分、尿嘧啶环和二磷酸基团取代的尿苷 5'-二磷酸 (UDP) 类似物，并测定了其对人 P2Y6 受体的活性。尿嘧啶环在 4 位上进行修饰，合成 4-取代的硫尿苷 5'-二磷酸类似物，以及在 2、3 和 5 位进行修饰。研究了磷酸链水平修饰的影响通过制备环状3',5'-二磷酸类似物、3'-二磷酸类似物和几种二核苷酸二磷酸。 5-Iodo-UDP 32 (EC50 = 0.15 microM) 与 UDP 等价，而 2'-羟基（氨基、叠氮基）的取代会大大降低效力。与 UDP 相比，2- 和 4- 硫代类似物分别为 20 和 21 也相对有效。然而，大多数其他修改大大降低了效力。分子模型表明，5'-UDP 和类似物的 β-磷酸对于与受体的三个保守阳离子残基中的两个建立静电相互作用至关重要。在4-硫醚衍生物中，4-乙硫基类似物23显示出0

  DOI：

  10.1021/jm060485n
• 作为产物：
  描述：

  4-硫-ump二钠盐 在 Meiothermus ruber polyphosphate kinase D₁₂₇S 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 生成 4-硫代-UDP
  参考文献：
  名称：

  10.1002/cctc.202400181

  摘要：

  AbstractPolyphosphate kinases (PPKs) are valuable biocatalysts for ATP cofactor regeneration as well as for the phosphorylation of non‐canonical nucleotides. The versatility of PPKs in the latter application is defined by their substrate scope. In this study, we investigate the substrate spectrum of the PPK2‐III enzyme from Meiothermus ruber (MrPPK) for the conversion of canonical and non‐canonical (deoxy)‐ribonucleotides. The enzyme shows high substrate promiscuity for purine and to minor degree pyrimidine substrates, with an overall preference for the native substrate AMP. With structure guided rational amino acid exchanges in the active site, we produced an MrPPK variant with improved activity for a broad variety of purine nucleotides. While the preference for AMP is lost, conversion of nucleotides without a 6‐amino function at the purine moiety is increased. This MrPPK variant is a versatile biocatalyst for the synthesis of non‐canonical nucleotides and could also be useful as a GTP cofactor regeneration system.

  DOI：

  10.1002/cctc.202400181

文献信息

• Certain dinucleotides and their use as modulators of mucociliary clearance and ciliary beat frequency
  申请人：——

  公开号：US20020082417A1

  公开（公告）日：2002-06-27

  The present invention relates to certain novel dinucleotides and formulations thereof which are highly selective agonists of the P2Y 2 and/or P2Y 4 purinergic receptor. They are useful in the treatment of chronic obstructive pulmonary diseases such as chronic bronchitis, PCD, cystic fibrosis, as well as prevention of pneumonia due to immobility. Furthermore, because of their general ability to clear retained mucus secretions and stimulate ciliary beat frequency, the compounds of the present invention are also useful in the treatment of sinusitis, otitis media and nasolacrimal duct obstruction. They are also useful for treatment of dry eye disease and retinal detachment as well as facilitating sputum induction and expectoration.

  本发明涉及某些新型二核苷酸及其制剂，它们是 P2Y 2 和/或 P2Y 4 嘌呤能受体的高选择性激动剂。它们可用于治疗慢性阻塞性肺部疾病，如慢性支气管炎、肺结核、囊性纤维化，以及预防因行动不便引起的肺炎。此外，由于本发明的化合物具有清除滞留的粘液分泌物和刺激纤毛跳动频率的一般能力，因此也可用于治疗鼻窦炎、中耳炎和鼻泪管阻塞。它们还可用于治疗干眼病和视网膜脱落，以及促进痰液的诱导和排出。
• DINUCLEOTIDES AND THEIR USES
  申请人：Inspire Pharmaceuticals, Inc.

  公开号：EP0981534A2

  公开（公告）日：2000-03-01
• NEUROPROTECTIVE IRON CHELATORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：TECHNION RESEARCH AND DEVELOPMENT FOUNDATION LTD.

  公开号：EP1565185A2

  公开（公告）日：2005-08-24
• Compositions, methods, kits and apparatus for determining the presence or absence of target molecules
  申请人：Q-RNA, INC.

  公开号：US20030180725A1

  公开（公告）日：2003-09-25

  The present invention is directed to methods, compositions, kits and apparatus to identify and detect the presence or absence of target analytes. The embodiments of the present invention have utility in medical diagnosis and analysis of various chemical compounds in specimens and samples, as well as the design of test kits and apparatus for implementing such methods.
• US4749647A
  申请人：——

  公开号：US4749647A

  公开（公告）日：1988-06-07