腺苷 5'-单氨基磷酸酯钠盐 | 6154-31-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 中文名称: 腺苷 5'-单氨基磷酸酯钠盐
• 中文别名: 腺苷5'-单氨基磷酸酯钠盐；腺苷-5ˊ-氨基磷酸钠盐
• 英文名称: AMP-Amidate
• 英文别名: adenosine 5'-monophosphoramidate；adenosine-5'-O-phosphoramidate；adenosine 5'-phosphoramidate；5'-AMPN；NH2-pA；[5']adenylic acid monoamide；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonamidic acid
• CAS: 6154-31-0
• 化学式: C₁₀H₁₅N₆O₆P
• 分子量: 346.239
• InChiKey: LDEMREUBLBGZBO-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 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：
  192
• 氢给体数：
  5
• 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'-adenylimidodiphosphate	32476-54-3	C10H16N6O9P2	426.219
  5'-腺嘌呤核苷酸	5'-adenosine monophosphate	61-19-8	C10H14N5O7P	347.224
  ——	SP-adenosine cyclic 3',5'-phosphramidate	100896-14-8	C10H13N6O5P	328.224
  腺苷三磷酸酯-gamma 酰胺	App(NH)p	58430-80-1	C10H17N6O12P3	506.199
  2,3-二乙酸腺苷酸酯	2',3'-di-O-acetyladenosine	29886-19-9	C14H17N5O6	351.319

• 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 5'-单氨基磷酸酯钠盐 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 氨 、 formamide 、 N,N'-二环己基碳二亚胺 、 叔丁醇 作用下， 生成 腺苷 5'-单氨基磷酸酯钠盐
  参考文献：
  名称：

  The Synthesis of Adenosine-5' and Uridine-5' Phosphoramidates

  摘要：

  DOI：

  10.1021/ja01547a072

文献信息

• Synthesis of Nucleoside Mono-, Di-, and Triphosphoramidates from Solid-Phase <i>cyclo</i>Saligenyl Phosphitylating Reagents
  作者：Yousef Ahmadibeni、Rakesh K. Tiwari、Gongqin Sun、Keykavous Parang

  DOI：10.1021/ol900320r

  日期：2009.5.21

  Subsequent reduction with borane solution produced polymer-bound 2-hydroxybenzyl alcohol. The reaction of immobilized 2-hydroxybenzyl alcohol with appropriate phosphitylating reagents yielded solid-phase cycloSaligenyl mono-, di-, and triphosphitylating reagents, which were reacted with unprotected nucleosides, followed by iodine oxidation, deprotection of cyanoethoxy groups, and the basic cleavage, respectively

  在碳酸钾的存在下，氯甲基聚苯乙烯树脂与 5-羟基水杨醛反应，得到聚合物结合的 2-羟基苯甲醛。随后用硼烷溶液还原产生聚合物结合的 2-羟基苯甲醇。固定化的 2-羟基苯甲醇与适当的亚磷酸酯化试剂反应生成固相环水杨基单-、二-和三亚磷酸酯化试剂，其与未保护的核苷反应，随后碘氧化、氰乙氧基脱保护和碱性裂解，分别以52-73% 的总产率提供 5'- O-核苷单-、二-和三氨基磷酸酯。
• 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。
• RNA CONTAINING COENZYMES, BIOTIN, OR FLUOROPHORES, AND METHODS FOR THEIR PREPARATION AND USE
  申请人：UNIVERSITY OF SOUTHERN MISSISSIPPI

  公开号：US20040241649A1

  公开（公告）日：2004-12-02

  Materials and methods for incorporating adenosine derivatives into the 5′ end of transcribed RNA are disclosed. Adenosine derivatives include naturally occurring compounds such as Coenzyme A, NAD, and FAD, as well as various non-naturally occurring compounds. The derivatives can be used to impart desirable properties to the RNA such as fluorescence, the ability to bind to receptors or ligands, and improved catalytic activity. The transcribed RNAs can be used in a variety of applications including nucleic acid detection, designed or random generation of catalytic RNAs, antisense applications, and in the study of RNA structure and function

  公开了将腺苷衍生物并入转录RNA 5'端的材料和方法。腺苷衍生物包括天然化合物，如辅酶A，NAD和FAD，以及各种非自然发生的化合物。这些衍生物可用于赋予RNA所需的性质，如荧光，与受体或配体结合的能力以及改善催化活性。转录的RNA可用于各种应用，包括核酸检测，设计或随机生成催化RNA，反义应用以及用于研究RNA结构和功能。
• DESIGN, SYNTHESIS AND USE OF SYNTHETIC NUCLEOTIDES COMPRISING CHARGE MASS TAGS
  申请人：QuantuMDx Group Limited

  公开号：US20160139133A1

  公开（公告）日：2016-05-19

  Embodiments of the present disclosure relate generally to reporter compositions which are synthetic nucleotides that comprise nucleotides with a high charge mass moiety attached thereto via a linker molecule. The linker molecules can vary in length in part to enable the high charge mass moiety to extend out from a DNA polymerase complex so that polymerization may not be influenced.

  本公开的实施例通常涉及记者组成物，其为合成核苷酸，包括通过连接分子连接到其上的具有高电荷质量部分的核苷酸。连接分子的长度可以不同，部分是为了使高电荷质量部分从DNA聚合酶复合物中延伸出来，以便不影响聚合作用。
• Novel azole dinucleotide compounds and methods for their production
  申请人：BRIGHAM YOUNG UNIVERSITY

  公开号：EP0090405A1

  公开（公告）日：1983-10-05

  A class of azole dinucleotide compounds of formula and the pharmaceutically acceptable salts of the compounds; wherein R is a heterocycle that is 3-carbamoyl-1,2,4-triazol-1-yl, 4-carbamoylthiazol-2-yl, or 4-carbamoylselenazol-2-yl and methods for their production are provided. Compounds of the class typically have pharmacological properties and are well tolerated, being useful, for example, in treating leukemias and solid tumors in warm blooded animals.

  一类式唑二核苷酸化合物及其药物可接受盐 其中 R 是 3-氨基甲酰基-1,2,4-三唑-1-基、4-氨基甲酰基噻唑-2-基或 4-氨基甲酰基硒唑-2-基的杂环。该类化合物通常具有药理特性，且耐受性良好，例如可用于治疗温血动物的白血病和实体瘤。