<6-amino-15N>adenine | 19713-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: <6-amino-15N>adenine
• 英文别名: adenine；<6-(15)N>adenine；<6'-15N>adenine；[6-15N]-adenine；[6-15N]adenine；7(9)H-purin-6-yl[¹⁵N]amine；7H-Purin-6-amine-15N；7H-purin-6-(15N)amine
• CAS: 19713-11-2
• 化学式: C₅H₅N₅
• 分子量: 136.121
• InChiKey: GFFGJBXGBJISGV-PTQBSOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <6-amino-15N>adenine 、 [1-14C]-D-ribose 在 adenylate kinase 、 pyruvate kinase adenine phosphoribosyltransferase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 phosphate buffer 为溶剂， 反应 16.0h， 生成 ((2R,3S,4R,5R)-5-(6-(amino-15N)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl-5-14C)methyl tetrahydrogen triphosphate
  参考文献：
  名称：

  E. 的过渡状态结构。大肠杆菌tRNA特异性腺苷脱氨酶

  摘要：

  细菌 tRNA 特异性腺苷脱氨酶 (TadA) 在 tRNA 的摆动位置催化腺苷基本脱氨为肌苷，并且是允许单个 tRNA 物种识别多个密码子所必需的。大肠杆菌 TadA 的过渡态结构通过动力学同位素效应 (KIE) 和量子化学计算进行表征。大肠杆菌 tRNA(Arg2) 的茎环用作最小化的 TadA 底物，其腺苷酸编辑位点同位素标记为 [1'-(3)H]、[5'-(3)H2]、[1 '-(14)C], [6-(13)C], [6-(15)N], [6-(13)C, 6-(15)N] 和 [1-(15)N] . [6-(13)C]-, [6-(15)N]-, [1-(15)N]-, [1'- 的本征 KIE 分别为 1.014、1.022、0.994、1.014 和 0.963 (3)H]-、[5'-(3)H2]-分别标记的底物。KIE 套件与具有完整的亲 S 面羟基攻击和几乎完整的 N1 质子化的晚期

  DOI：

  10.1021/ja078008x
• 作为产物：
  描述：

  6-氯嘌呤 在 15N-氨 作用下， 以 甲醇 、 水 为溶剂， 120.0 ℃ 、206.84 kPa 条件下， 反应 5.0h， 生成 <6-amino-15N>adenine
  参考文献：
  名称：

  An improved synthesis of [amino-15N]adenine; useful in the large scale synthesis of 2′-deoxy[amino-15N]adenosine

  摘要：

  2′-脱氧[氨基-15N]腺苷是利用市场上可买到的起始材料分两步制成的。这些反应经放大后可得到 5 克批量的标记材料。

  DOI：

  10.1002/jlcr.2580360704

文献信息

• An improved synthesis of [amino-15N]adenine; useful in the large scale synthesis of 2′-deoxy[amino-15N]adenosine
  作者：Joe Kelly、David A. Ashburn、Ryszard Michalczyk、Louis A. Silks

  DOI：10.1002/jlcr.2580360704

  日期：1995.7

  2′-Deoxy[Amino-15N]Adenosine has been constructed in two steps from commercially available starting materials. These reactions have been scaled up to give 5 gram lots of labeled material.

  2′-脱氧[氨基-15N]腺苷是利用市场上可买到的起始材料分两步制成的。这些反应经放大后可得到 5 克批量的标记材料。
• Synthesis of multiply labelled ribonucleosides for sequence-specific labelling of oligo-RNA
  作者：Jan Milecki、Andras Földesi、Artur Fischer、Ryszard W. Adamiak、Jyoti Chattopadhyaya

  DOI：10.1002/jlcr.503

  日期：2001.10.15

  The synthesis of ribonucleotide blocks multiply labelled with 2H, 13C and 15N for solid support synthesis of sequence specifically labelled RNA is described. Labels were introduced in the ribose ring (13C), C5 position of pyrimidine nucleobases (2H) and exocyclic amino groups (15N) and serve as multiple probes for studying the various physicochemical consequences of physiologically important RNA folding by high-resolution multi-nuclear NMR spectroscopy. Copyright © 2001 John Wiley & Sons, Ltd.

  本文描述了核糖核苷酸块与2H、13C和15N的复合标记，用于序列特异性标记的RNA的固体支持合成。标记被引入核糖环（13C）、嘧啶核苷酸的C5位（2H）和外环氨基（15N），并作为多重探针，用于通过高分辨率多核核磁共振光谱研究生理上重要的RNA折叠的各种物理化学后果。版权所有 © 2001 John Wiley & Sons, Ltd.
• Sequence-specific cleavage of DNA by N-bromoacetyldistamycin. Product and kinetic analyses
  作者：Brenda F. Baker、Peter B. Dervan

  DOI：10.1021/ja00189a054

  日期：1989.3

  N-Bromoacetyldistamycin (BO) is a designed molecule with two structural domains with distinct functions: sequence specific binding to double helical DNA and cleavage of the DNA backbone. An electrophilic bromoacetyl group is appended to the amino end of the tripeptide from the natural product distamycin A. Footprinting studies reveal that N-bromoacetyldistamycin binds within minutes to a 167 base pair

  N-溴乙酰双霉素 (BO) 是一种设计好的分子，具有两个具有不同功能的结构域：与双螺旋 DNA 的序列特异性结合和 DNA 主链的切割。亲电溴乙酰基团附加到来自天然产物多他霉素 A 的三肽的氨基末端。 足迹研究表明，N-溴乙酰双霉素在几分钟内与 167 个碱基对 (bp) 限制性片段结合，位于四个富含 A、T 的位点 5 个碱基对尺寸为 5'-TTTAA、GTTTA、AAATT 和 GAAAT-3'。在 37 °C 下反应 5 小时后，该 167 bp 限制性片段中 GTTTA 位点的单个腺嘌呤处发生切割，并遵循哌啶处理程序。BD 的共价连接发生在腺嘌呤的 N3。3-（乙酰基二霉素）腺嘌呤是 BD 与 15 碱基对寡核苷酸双链体 5'-CGGTAGTTTATCACA-3' 在 37 °C 下反应释放的产物。哌啶处理后切割位点的 3' 和 5' DNA 末端是磷酸基团。BD 对双链 DNA
• Mass spectrometry of nucleic acid constituents. Electron ionization spectra of selectively labeled adenines
  作者：Satinder Sethi、S. P. Gupta、E. E. Jenkins、C. W. Whitehead、Leroy B. Townsend、James A. McCloskey

  DOI：10.1021/ja00376a017

  日期：1982.6
• Transition-State Variation in Human, Bovine, and <i>Plasmodium falciparum</i> Adenosine Deaminases
  作者：Minkui Luo、Vipender Singh、Erika A. Taylor、Vern L. Schramm

  DOI：10.1021/ja072122y

  日期：2007.6.1

  Adenosine deaminases (ADAs) from human, bovine, and Plasmodium falciparum sources were analyzed by kinetic isotope effects (KIEs) and shown to have distinct but related transition states. Human adenosine deaminase (HsADA) is present in most mammalian cells and is involved in B- and T-cell development. The ADA from Plasmodium falciparum (PfADA) is essential in this purine auxotroph, and its inhibition is expected to have therapeutic effects for malaria. Therefore, ADA is of continuing interest for inhibitor design. Stable structural mimics of ADA transition states are powerful inhibitors. Here we report the transition-state structures of PfADA, HsADA, and bovine ADA (BtADA) solved using competitive kinetic isotope effects (KIE) and density functional calculations. Adenines labeled at [6-C-13], [6-N-15], [6-C-13, 6-N-15], and [1-N-15] were synthesized and enzymatically coupled with [1'-C-14] ribose to give isotopically labeled adenosines as ADA substrates for KIE analysis. [6-C-13], [6-N-15], and [1-N-15]adenosines reported intrinsic KIE values of (1.010, 1.011, 1.009), (1.005, 1.005, 1.002), and (1.004, 1.001, 0.995) for PfADA, HsADA, and BtADA, respectively. The differences in intrinsic KIEs reflect structural alterations in the transition states. The [1-N-15] KIEs and computational modeling results indicate that PfADA, HsADA, and BtADA adopt early SNAr transition states, where N1 protonation is partial and the bond order to the attacking hydroxyl nucleophile is nearly complete. The key structural variation among PfADA, HsADA, and BtADA transition states lies in the degree of N1 protonation with the decreased bond lengths of 1.92, 1.55, and 1.28 angstrom, respectively. Thus, PfADA has the earliest and BtADA has the most developed transition state. This conclusion is consistent with the 20-36-fold increase of k(cat) in comparing PfADA with HsADA and BtADA.