腺苷单氟磷酸盐 | 19375-33-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 腺苷单氟磷酸盐
• 英文名称: adenosine 5'-phosphorofluoride
• 英文别名: adenosine 5'-phosphofluoride；F-pA；[5']adenylyl fluoride；Fluorphosphorsaeure-mono-5'-adenosylester；Monofluorophosphorsaeure-5'-adenosylester；Adenosin-5'-monofluorphosphat；Adenosine monophosphofluoridate；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-fluorophosphinic acid
• CAS: 19375-33-8
• 化学式: C₁₀H₁₃FN₅O₆P
• 分子量: 349.215
• InChiKey: PZWOGYWWDIXJIB-KQYNXXCUSA-N

物化性质

• 沸点：
  728.7±70.0 °C(Predicted)
• 密度：
  2.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  11

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5'-腺嘌呤核苷酸	5'-adenosine monophosphate	61-19-8	C10H14N5O7P	347.224
  5’-三磷酸腺苷	ATP	56-65-5	C10H16N5O13P3	507.184
  ——	adenosine 5'-phosphorimidazolide	20816-58-4	C13H16N7O6P	397.287

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  5'-腺嘌呤核苷酸	5'-adenosine monophosphate	61-19-8	C10H14N5O7P	347.224
  二磷酸腺苷	adenosine 5'-diphosphate	58-64-0	C10H15N5O10P2	427.204

反应信息

• 作为反应物：
  描述：

  腺苷单氟磷酸盐 在 Arabidopsis thaliana Hint₄ 作用下， 生成 二磷酸腺苷
  参考文献：
  名称：

  Dual activity of certain HIT-proteins:A. thalianaHint4 andC. elegansDcpS act on adenosine 5′-phosphosulfate as hydrolases (forming AMP) and as phosphorylases (forming ADP)

  摘要：

  Histidine triad (HIT)‐family proteins interact with different mono‐ and dinucleotides and catalyze their hydrolysis. During a study of the substrate specificity of seven HIT‐family proteins, we have shown that each can act as a sulfohydrolase, catalyzing the liberation of AMP from adenosine 5′‐phosphosulfate (APS or SO4‐pA). However, in the presence of orthophosphate, Arabidopsis thaliana Hint4 and Caenorhabditis elegans DcpS also behaved as APS phosphorylases, forming ADP. Low pH promoted the phosphorolytic and high pH the hydrolytic activities. These proteins, and in particular Hint4, also catalyzed hydrolysis or phosphorolysis of some other adenylyl‐derivatives but at lower rates than those for APS cleavage. A mechanism for these activities is proposed and the possible role of some HIT‐proteins in APS metabolism is discussed.

  DOI：

  10.1016/j.febslet.2009.11.003
• 作为产物：
  描述：

  5'-腺嘌呤核苷酸 在 potassium fluoride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 为溶剂， 生成 腺苷单氟磷酸盐
  参考文献：
  名称：

  使用氟离子水溶液和水溶性碳二亚胺引入P-F键：一种简便的替代合成方法，氟化磷和膦酰氟

  摘要：

  核糖核苷酸和其他磷酸盐的化学作用得以扩展，以包括它们在水溶性碳二亚胺存在下与氟化钾在水溶液中的反应。形成了高产率（＞ 98％）的氟代磷酸酯。HPLC，质谱和NMR的组合证实了产品的身份。该方法以同样令人满意的结果应用于具有生理活性的膦酸酯Adefovir®和Tenofovir®，从而提供了新的化合物。报道了新的膦酰氟的详细的NMR研究。

  DOI：

  10.1016/j.tetlet.2015.07.036

文献信息

• The reaction of activated RNA species with aqueous fluoride ion: a convenient synthesis of nucleotide 5′-phosphorofluoridates and a note on the mechanism
  作者：Michael F. Aldersley、Prakash C. Joshi、Herbert M. Schwartz、Anthony J. Kirby

  DOI：10.1016/j.tetlet.2014.01.051

  日期：2014.2

  The chemistry of 5′-phosphorimidazolides of ribonucleosides is extended to include their reaction with alkali metal fluorides in aqueous solution. High yields of 5′-phosphorofluoridates are formed, especially with potassium fluoride, but no detectable oligomerization products were formed. A combination of HPLC, mass spectrometry, synthesis, kinetics, and NMR confirms the identities of the products

  核糖核苷的5'-磷酰胺基咪唑化物的化学作用得以扩展，包括它们与水溶液中的碱金属氟化物的反应。形成了高产率的5'-氟代磷酸酯，尤其是氟化钾，但未形成可检测到的低聚产物。HPLC，质谱，合成，动力学和NMR的结合证实了产物的身份。适当控制pH值可在较短的反应时间内获得更高的收率。该新方法与涉及非水化学或带有三磷酸核苷酸的水化学的其他合成路线形成了鲜明的对比。
• Recognition of different nucleotidyl-derivatives as substrates of reactions catalyzed by various HIT-proteins
  作者：Andrzej Guranowski、Anna Maria Wojdyła、Jarosław Zimny、Anna Wypijewska、Joanna Kowalska、Maciej Łukaszewicz、Jacek Jemielity、Edward Darżynkiewicz、Agata Jagiełło、Paweł Bieganowski

  DOI：10.1039/b9nj00660e

  日期：——

  Proteins that have a histidine triad in their active sites belong to the HIT-protein superfamily. They are ubiquitous, are involved in the metabolism of different nucleotides and catalyze their hydrolysis and/or phosphorolysis liberating either the corresponding 5′-NMP or 5′-NDP, respectively. We studied substrate specificity of nine recombinant HIT-proteins with adenosine 5′-phosphosulfate (1), adenosine 5′-phosphoramidate (2), adenosine 5′-phosphorothioate (3), adenosine 5′-phosphorofluoride (4), diadenosine 5′,5′′′-P1,P3-triphosphate (5), di(7-methylguanosine) 5′,5′′′-P1,P3-triphosphate (6) and adenosine 5′-hypophosphate (7). Preferences for the recognition of these compounds as substrates by individual proteins differed. All the proteins hydrolyzed (1) but the Arabidopsis thaliana Hint1 did it very slowly. None of the proteins cleaved (7). Only A. thaliana Hint1 and Escherichia coli HinT hydrolyzed (3). Three proteins known as dinucleoside triphosphatases, human and A. thaliana Fhit-proteins and Trypanosoma brucei HIT-45, cleaved (1), (2), (4), (5) and (6). Caenorhabditis elegans decapping protein DcpS degraded (1), (5), (6) and poorly (4). A. thaliana aprataxin-like protein and Hint4 hydrolyzed only (1), (2) and (4), in that order of efficiency. Velocities of those reactions and some Km values were determined. Applicability of this study to the metabolism of certain nucleotidyl-derivatives is discussed.

  活性位点具有组氨酸三联体的蛋白质属于 HIT 蛋白质超家族。它们无处不在，参与不同核苷酸的代谢并催化它们的水解和/或磷酸解，分别释放相应的 5'-NMP 或 5'-NDP。我们研究了九种重组 HIT 蛋白的底物特异性，其中包括腺苷 5'-磷酸硫酸酯 (1)、腺苷 5'-氨基磷酸酯 (2)、腺苷 5'-硫代磷酸酯 (3)、腺苷 5'-氟化磷 (4)、二腺苷 5' ,5'''-P1,P3-三磷酸 (5)、二(7-甲基鸟苷) 5',5'''-P1,P3-三磷酸 (6) 和腺苷 5'-连二磷酸 (7)。各个蛋白质对这些化合物作为底物的识别偏好不同。所有蛋白质都会水解 (1)，但拟南芥 Hint1 的水解速度非常缓慢。没有蛋白质被裂解 (7)。仅拟南芥 Hint1 和大肠杆菌 HinT 会水解 (3)。被称为二核苷三磷酸酶、人类和拟南芥 Fhit 蛋白以及布氏锥虫 HIT-45 的三种蛋白质被切割 (1)、(2)、(4)、(5) 和 (6)。秀丽隐杆线虫脱帽蛋白 DcpS 降解 (1)、(5)、(6) 和较差 (4)。拟南芥 aprataxin 样蛋白和 Hint4 按效率顺序仅水解 (1)、(2) 和 (4)。确定了这些反应的速度和一些 Km 值。讨论了本研究对某些核苷酸衍生物代谢的适用性。
• The introduction of P–F bonds using aqueous fluoride ion and a water soluble carbodiimide: a convenient alternative synthesis of phosphorofluoridates and phosphonofluoridates
  作者：Michael F. Aldersley、Prakash C. Joshi、Elizabeth L. Ott、Scott A. McCallum、Anthony J. Kirby

  DOI：10.1016/j.tetlet.2015.07.036

  日期：2015.9

  The chemistry of ribonucleotides and other phosphates is extended to include their reactions with potassium fluoride in aqueous solution in the presence of a water soluble carbodiimide. High yields (>98%) of phosphorofluoridates are formed. A combination of HPLC, mass spectrometry, and NMR confirms the identities of the products. The methodology is applied, with equally satisfactory outcomes, to the

  核糖核苷酸和其他磷酸盐的化学作用得以扩展，以包括它们在水溶性碳二亚胺存在下与氟化钾在水溶液中的反应。形成了高产率（＞ 98％）的氟代磷酸酯。HPLC，质谱和NMR的组合证实了产品的身份。该方法以同样令人满意的结果应用于具有生理活性的膦酸酯Adefovir®和Tenofovir®，从而提供了新的化合物。报道了新的膦酰氟的详细的NMR研究。
• Dual activity of certain HIT-proteins:<i>A. thaliana</i>Hint4 and<i>C. elegans</i>DcpS act on adenosine 5′-phosphosulfate as hydrolases (forming AMP) and as phosphorylases (forming ADP)
  作者：Andrzej Guranowski、Anna Maria Wojdyła、Jarosław Zimny、Anna Wypijewska、Joanna Kowalska、Jacek Jemielity、Richard E. Davis、Paweł Bieganowski

  DOI：10.1016/j.febslet.2009.11.003

  日期：2010.1.4

  Histidine triad (HIT)‐family proteins interact with different mono‐ and dinucleotides and catalyze their hydrolysis. During a study of the substrate specificity of seven HIT‐family proteins, we have shown that each can act as a sulfohydrolase, catalyzing the liberation of AMP from adenosine 5′‐phosphosulfate (APS or SO4‐pA). However, in the presence of orthophosphate, Arabidopsis thaliana Hint4 and Caenorhabditis elegans DcpS also behaved as APS phosphorylases, forming ADP. Low pH promoted the phosphorolytic and high pH the hydrolytic activities. These proteins, and in particular Hint4, also catalyzed hydrolysis or phosphorolysis of some other adenylyl‐derivatives but at lower rates than those for APS cleavage. A mechanism for these activities is proposed and the possible role of some HIT‐proteins in APS metabolism is discussed.