adenosine 5'-phosphoramidate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: adenosine 5'-phosphoramidate
• 英文别名: Adenosine 5'-phosphoramidate(1-)；amino-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]phosphinate
• 化学式: C₁₀H₁₄N₆O₆P
• 分子量: 345.232
• InChiKey: LDEMREUBLBGZBO-KQYNXXCUSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 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：
  195
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  adenosine 5'-phosphoramidate 在 盐酸 作用下， 反应 8.0h， 生成 5'-腺嘌呤核苷酸
  参考文献：
  名称：

  腺苷环3'，5'-（R P）-和（S P）-磷酸氨基甲酸酯，核苷环状3'，5'-磷酰胺的第一代表

  摘要：

  腺苷环3'，5'-磷酸氨基甲酸酯的合成方法是：将腺苷环3'，5'-磷酸与POCl 3在磷酸三甲酯中于0°C反应1小时，然后用悬浮液原位处理反应混合物。 （NH 4）2 CO 3在无水DMF或吡啶或DMF /吡啶混合物中在25°C下放置30分钟。非对映异构体（P）-和（P）-的相对量取决于（NH 4）2的溶剂通过反相分配色谱分离CO 3处理。（R P）-和（S的水解P）-继续进行（在0.1 N HCl中为90％，在0.1 N NaOH中为100％）-POC键断裂。

  DOI：

  10.1016/s0040-4039(00)98869-5
• 作为产物：
  描述：

  R_P-adenosine cyclic 3',5'-phosphoramidate 在 sodium hydroxide 作用下， 反应 0.02h， 以70.2%的产率得到Adenosine 2',3'-cyclic monophosphonate
  参考文献：
  名称：

  腺苷环3'，5'-（R P）-和（S P）-磷酸氨基甲酸酯，核苷环状3'，5'-磷酰胺的第一代表

  摘要：

  腺苷环3'，5'-磷酸氨基甲酸酯的合成方法是：将腺苷环3'，5'-磷酸与POCl 3在磷酸三甲酯中于0°C反应1小时，然后用悬浮液原位处理反应混合物。 （NH 4）2 CO 3在无水DMF或吡啶或DMF /吡啶混合物中在25°C下放置30分钟。非对映异构体（P）-和（P）-的相对量取决于（NH 4）2的溶剂通过反相分配色谱分离CO 3处理。（R P）-和（S的水解P）-继续进行（在0.1 N HCl中为90％，在0.1 N NaOH中为100％）-POC键断裂。

  DOI：

  10.1016/s0040-4039(00)98869-5

文献信息

• Purification and properties of adenylyl sulphate:ammonia adenylyltransferase from <i>Chlorella</i> catalysing the formation of adenosine 5′-phosphoramidate from adenosine 5′-phosphosulphate and ammonia
  作者：Heinz Fankhauser、Jerome A. Schiff、Leonard J. Garber

  DOI：10.1042/bj1950545

  日期：1981.6.1

  species) is about 10mm. A large variety of primary, secondary and tertiary amines or amides will not replace ammonia. One mol.prop. of adenosine 5'-phosphosulphate reacts with 1 mol.prop. of ammonia to yield 1 mol.prop. each of adenosine 5'-phosphoramidate and sulphate; no AMP is found. The highly purified enzyme does not catalyse any of the known reactions of adenosine 5'-phosphosulphate, including

  小球藻小球藻的提取物。细菌，菠菜，大麦，盘基网柄菌和大肠杆菌在氨存在下由5'-磷酸腺苷酶促地形成未知化合物。该未知化合物与5'-氨基磷酸腺苷具有以下特性：组成部分的摩尔比例（1腺嘌呤：1核糖：1磷酸盐：1在低pH下释放的氨），在所有测试的缓冲液（包括硼酸盐）中进行共电泳，形成AMP在低pH条件下，通过释放氨，质谱和红外光谱并通过磷酸二酯酶转化为5'-AMP来实现。因此，该未知化合物似乎与5'-氨基磷酸腺苷相同。催化氨和5'腺苷形成5'-氨基磷酸腺苷的酶 -磷酸通过使用（NH（4））（2）SO（4）沉淀和DEAE-纤维素，Sephadex和活性蓝2-琼脂糖层析从小球藻中纯化1800倍（至均一）。纯化的酶在聚丙烯酰胺凝胶电泳上对应于60000-65000分子量的位置上显示出一条与活性相符的蛋白质带，并在十二烷基硫酸钠/聚丙烯酰胺凝胶电泳上产生26000、21000和17000分子的三个亚基重量
• Adenosine Monophosphoramidase Activity of Hint and Hnt1 Supports Function of Kin28, Ccl1, and Tfb3
  作者：Pawel Bieganowski、Preston N. Garrison、Santosh C. Hodawadekar、Gerard Faye、Larry D. Barnes、Charles Brenner

  DOI：10.1074/jbc.m111480200

  日期：2002.3

  The histidine triad superfamily of nucleotide hydrolases and nucleotide transferases consists of a branch of proteins related to Hint and Aprataxin, a branch of Fhit-related hydrolases, and a branch of galactose-1-phosphate uridylyltransferase (GalT)-related transferases. Although substrates of Fhit and GalT are known and consequences of mutations in Aprataxin, Fhit, and GalT are known, good substrates had not been reported for any member of the Hint branch, and mutational consequences were unknown for Hint orthologs, which are the most ancient and widespread proteins in the Hint branch and in the histidine triad superfamily. Here we show that rabbit and yeast Hint hydrolyze the natural product adenosine-5'-monophosphoramidate (AMPNH(2)) in an active-site-dependent manner at second order rates exceeding 1,000,000 M-1 S-1. Yeast strains constructed with specific loss of the Hntl active site fail to grow on galactose at elevated temperatures. Loss of Hntl enzyme activity also leads to hypersensitivity to mutations in Cell, Tfb3, and Kin28, which constitute the TFIIK kinase subcomplex of general transcription factor TFIIH and to mutations in Cak1, which phosphorylates Kin28. The target of Hnt1 regulation in this pathway was shown to be downstream of Cak1 and not to affect stability of Kin28 monomers. Functional complementation of all Hnt1 phenotypes was provided by rabbit Hint, which is only 22% identical to yeast Hntl but has very similar adenosine monophosphoramidase activity.
• 31P NMR and Genetic Analysis Establish hinT as the Only Escherchia coli Purine Nucleoside Phosphoramidase and as Essential for Growth under High Salt Conditions
  作者：Tsui-Fen Chou、Pawel Bieganowski、Kara Shilinski、Jilin Cheng、Charles Brenner、Carston R. Wagner

  DOI：10.1074/jbc.m500434200

  日期：2005.4

  Eukaryotic cells encode AMP-lysine (AMP-N-epsilon-(N-alpha-acetyl lysine methyl ester) 5'-phosphoramidate) hydrolases related to the rabbit histidine triad nucleotide-binding protein 1 (Hint1) sequence. Bacterial and archaeal cells have Hint homologs annotated in a variety of ways, but the enzymes have not been characterized, nor have phenotypes been described due to loss of enzymatic activity. We developed a quantitative P-31 NMR assay to determine whether Escherichia coli possesses an adenosine phosphoramidase activity. Indeed, soluble lysates prepared from wild-type laboratory E. coli exhibited activity on the model substrate adenosine 5'-monophosphoramidate (AMP-NH2). The E. coli Hint homolog, which had been comprehensively designated ycfF and is here named hinT, was cloned, overexpressed, purified, and characterized with respect to purine nucleoside phosphoramidate substrates. Bacterial hinT was several times more active than human or rabbit Hint1 on five model substrates. In addition, bacterial and mammalian enzymes preferred guanosine versus adenosine phosphoramidates as substrates. Analysis of the lysates from a constructed hinT knock-out strain of E. coli demonstrated that all of the cellular purine nucleoside phosphoramidase activity is due to hinT. Physiological analysis of this mutant revealed that the loss of hinT results in failure to grow in media containing 0.75 M KCl, 0.9 M NaCl, 0.5 M NaOAc, or 10 mM MnCl2. Thus, cation-resistant bacterial cell growth may be dependent on the hydrolysis of adenylylated and/or guanylylated phosphoramidate substrates by hinT.