uridine 5'-(β,γ-methylene)triphosphate | 71850-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: uridine 5'-(β,γ-methylene)triphosphate
• 英文别名: Uridine 5'-monophosphate, monoanhydride with (phosphonomethyl)phosphonic acid；[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methylphosphonic acid
• CAS: 71850-06-1
• 化学式: C₁₀H₁₇N₂O₁₄P₃
• 分子量: 482.171
• InChiKey: YAMUBYIKSYFVRX-ZOQUXTDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  250
• 氢给体数：
  7
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  lysyl adenylate 、 uridine 5'-(β,γ-methylene)triphosphate 在 zinc(II) chloride 作用下， 以40%的产率得到adenosine(uridine) 5',5'''-P¹,P⁴-(β,γ-methylene)tetraphosphate
  参考文献：
  名称：

  Characterisation of stress protein LysU. Enzymic synthesis of diadenosine 5′,5‴-P¹,P⁴-tetraphosphate (Ap₄A) analogues by LysU

  摘要：

  The stress protein LysU (lysyl tRNA synthetase) has been purified from a recombinant strain of Escherichia coli expressing the plasmid pXLys5, and kinetically characterised. Preparative syntheses of analogues of the biologically important molecule diadenosine 5',5'''-P-1,P-4-tetraphosphate (Ap(4)A) are then achieved in good yield by enzyme catalysis, using purified LysU.

  DOI：

  10.1039/p19960002009

文献信息

• The effect of bisphosphonate acidity on the activity of a thymidylyltransferase
  作者：Stephen A. Beaton、Patricia M. Jiang、Jonathan C. Melong、Matthew W. Loranger、Samy Mohamady、Thomas I. Veinot、David L. Jakeman

  DOI：10.1039/c3ob41017j

  日期：——

  Thymidylyltransferases (thymidine diphospho pyrophosphorylases) are nucleotidylyltransferases that play key roles in the biosynthesis of carbohydrate components within bacterial cell walls and in the biosynthesis of glycosylated natural products. They catalyze the formation of sugar nucleotides concomitant with the release of pyrophosphate. Protein engineering of thymidylyltransferases has been an approach for the production of a variety of non-physiological sugar nucleotides. In this work, we have explored chemical approaches towards modifying the activity of the thymidylyltransferase (Cps2L) cloned from S. pneumoniae, through the use of chemically synthesized ‘activated’ nucleoside triphosphates with enhanced leaving groups, or by switching the metal ion co-factor specificity. Within a series of phosphonate-containing nucleoside triphosphate analogues, thymidylyltransferase activity is enhanced based on the acidity of the leaving group and a Brønsted-type analysis indicated that leaving group departure is rate limiting. We have also determined IC50 values for a series of bisphosphonates as inhibitors of thymidylyltransferases. No correlation between the acidity of the inhibitors (pKa) and the magnitude of enzyme inhibition was found.

  胸苷酰转移酶（胸苷二磷酸焦磷酸化酶）是一种核苷酸转移酶，在细菌细胞壁内碳水化合物成分的生物合成以及糖基化天然产物的生物合成中发挥着关键作用。它们在催化糖核苷酸形成的同时释放焦磷酸。胸苷基转移酶的蛋白质工程是生产各种非生理糖核苷酸的一种方法。在这项工作中，我们通过使用化学合成的具有增强离去基团的 "活化 "三磷酸核苷，或通过改变金属离子辅助因子的特异性，探索了改变从肺炎双球菌克隆的胸苷基转移酶（Cps2L）活性的化学方法。在一系列含膦酸盐的三磷酸核苷类似物中，胸腺苷酸转移酶的活性根据离去基团的酸度而增强，布氏分析表明离去基团的离去是限制速率的。我们还测定了作为胸腺苷酸转移酶抑制剂的一系列双膦酸盐的 IC50 值。我们没有发现抑制剂的酸性（pKa）与酶抑制作用的大小之间有任何关联。
• 4,5-Dicyanoimidazole-promoted synthesis of dinucleoside polyphosphates and their analogs
  作者：Qi Sun、Shan-Shan Gong、Si Liu、Jian Sun、Guo-Dong Liu、Cha Ma

  DOI：10.1016/j.tet.2014.05.013

  日期：2014.7
• Characterisation of stress protein LysU. Enzymic synthesis of diadenosine 5′,5‴-P¹,P⁴-tetraphosphate (Ap₄A) analogues by LysU
  作者：Maria-Elena Theoclitou、E. Pernilla L. Wittung、Alison D. Hindley、Talal S. H. El-Thaher、Andrew D. Miller

  DOI：10.1039/p19960002009

  日期：——

  The stress protein LysU (lysyl tRNA synthetase) has been purified from a recombinant strain of Escherichia coli expressing the plasmid pXLys5, and kinetically characterised. Preparative syntheses of analogues of the biologically important molecule diadenosine 5',5'''-P-1,P-4-tetraphosphate (Ap(4)A) are then achieved in good yield by enzyme catalysis, using purified LysU.