8-¹³C-adenine | 86967-48-8

• 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: 8-¹³C-adenine
• 英文别名: 1H-Purin-6-amine-8-13C；7H-purin-6-amine
• CAS: 86967-48-8
• 化学式: C₅H₅N₅
• 分子量: 136.117
• InChiKey: GFFGJBXGBJISGV-OUBTZVSYSA-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：

  8-¹³C-adenine 在 sodium methylate 、 苯甲酰氯 作用下， 生成 13C(8)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and Utilization of¹³C(8)-Enriched Purines

  摘要：

  A new and more efficient method is presented for the synthesis of 13C(8)-enriched adenine. In addition, we present for the first time the synthesis of 13C(8)-enriched 2-aminopurine and purine. All three analogues have been converted to the corresponding ribonucleosides. The adenine analogue has been further converted to the 2'-deoxy-nucleoside and incorporated into a synthetic oligonucleotide. Data is presented demonstrating the utility of 13C-enrichment in heteronuclear isotope-edited NMR spectra.

  DOI：

  10.1080/07328319908045591
• 作为产物：
  描述：

  N-(4,6-diaminopyrimidin-5-yl)formamide 在 ammonium hydroxide 、 乙酸酐 作用下， 生成 8-¹³C-adenine
  参考文献：
  名称：

  Synthesis and Utilization of¹³C(8)-Enriched Purines

  摘要：

  A new and more efficient method is presented for the synthesis of 13C(8)-enriched adenine. In addition, we present for the first time the synthesis of 13C(8)-enriched 2-aminopurine and purine. All three analogues have been converted to the corresponding ribonucleosides. The adenine analogue has been further converted to the 2'-deoxy-nucleoside and incorporated into a synthetic oligonucleotide. Data is presented demonstrating the utility of 13C-enrichment in heteronuclear isotope-edited NMR spectra.

  DOI：

  10.1080/07328319908045591

文献信息

• Excited States of Nucleic Acids Probed by Proton Relaxation Dispersion NMR Spectroscopy
  作者：Michael Andreas Juen、Christoph Hermann Wunderlich、Felix Nußbaumer、Martin Tollinger、Georg Kontaxis、Robert Konrat、D. Flemming Hansen、Christoph Kreutz

  DOI：10.1002/anie.201605870

  日期：2016.9.19

  was previously shown to undergo a two site exchange process in the micro- to millisecond time regime. Using proton relaxation dispersion experiments the exchange parameters determined earlier could be recapitulated, thus validating the proposed approach. We further investigated the dynamics of the cTAR DNA, a DNA transcript that is involved in the viral replication cycle of HIV-1. Again, an exchange

  在这项工作中，引入了一种改进的核酸稳定同位素标记方案。新颖的构建模块消除/最小化同核 (13) C 和 (1) H 标量耦合，从而允许质子弛豫分散 (RD) 实验准确报告核酸的化学交换。使用位点特异性 (2) H 和 (13) C 标记，将自旋拓扑引入 DNA 和 RNA 中，使 (1) H 弛豫分散实验能够以简单的方式应用。新型 RNA/DNA 构建模块已成功整合到两种核酸中。先前显示 A 位点 RNA 在微秒至毫秒的时间内经历了两个位点交换过程。使用质子弛豫色散实验，可以概括之前确定的交换参数，从而验证所提出的方法。我们进一步研究了 cTAR DNA 的动力学，cTAR DNA 是一种参与 HIV-1 病毒复制周期的 DNA 转录物。同样，交换过程可以被表征和量化。这显示了新标记方案对于(1)核酸HRD实验的普遍适用性。
• Synthesis of an adenine N-3 substituted CBI adduct by alkylation of adenine with a 1-iodomethylindoline seco-CBI precursor
  作者：Alban J. Allentoff、Michael A. Wallace、Sarah C. Traeger、Naiyu Zheng、Qian Zhang、Samuel J. Bonacorsi

  DOI：10.1016/j.tet.2018.09.057

  日期：2018.11

  The synthesis of a 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI)-adenine adduct via regioselective N-3 alkylation of adenine with a 1-(iodomethyl)-2,3-dihydro-1H-benzo[e]indol-5-ol (I-seco-CBI)-containing precursor is described. Spectroscopic analyses of the unlabeled and adenine-C8 carbon-13 labeled adducts utilizing ROESY NMR techniques allowed structural assignment of the alkylation product

  通过1-（碘甲基）-2,3对腺嘌呤的区域选择性N-3烷基化反应合成1,2,9,9a-四氢环丙烷[ c ]苯并[e]吲哚-4-酮（CBI）-腺嘌呤加合物-二氢-1 H描述了含-苯并[e]吲哚-5-醇（I-seco-CBI）的前体。利用ROESY NMR技术对未标记和腺嘌呤-C8碳13标记的加合物进行光谱分析，可以烷基化产物作为腺嘌呤N-3取代的区域异构体进行结构分配。通过此方法，还制备了含有六个碳13标记的N-3加合物的稳定同位素标记版本，用作LC-MS内标。还发现该环化的含CB​​I的化合物在升高的温度下将腺嘌呤烷基化以产生N-3加合物，尽管其速率比I-seco-CBI前体的速率明显降低。用I-seco-CBI前体进行腺嘌呤烷基化可轻松获得CBI-腺嘌呤加合物的可扩展性和便捷性，从而使其可作为开发基于杜卡霉素的ADC的功效标记。
• Chemo-enzymatic synthesis of site-specific isotopically labeled nucleotides for use in NMR resonance assignment, dynamics and structural characterizations
  作者：Andrew P. Longhini、Regan M. LeBlanc、Owen Becette、Carolina Salguero、Christoph H. Wunderlich、Bruce A. Johnson、Victoria M. D'Souza、Christoph Kreutz、T. Kwaku Dayie

  DOI：10.1093/nar/gkv1333

  日期：2016.4.7

  Stable isotope labeling is central to NMR studies of nucleic acids. Development of methods that incorporate labels at specific atomic positions within each nucleotide promises to expand the size range of RNAs that can be studied by NMR. Using recombinantly expressed enzymes and chemically synthesized ribose and nucleobase, we have developed an inexpensive, rapid chemo-enzymatic method to label ATP and

  稳定的同位素标记是核酸NMR研究的核心。在每个核苷酸内特定原子位置掺入标记的方法的开发有望扩大可通过NMR研究的RNA的大小范围。使用重组表达的酶和化学合成的核糖和核碱基，我们开发了一种廉价，快速的化学酶促方法，可以特异性地标记ATP和GTP位点，且产率高达90％。我们使用体外转录将这些核苷酸整合到大小为27至59个核苷酸的RNA中：A-位点（27 nt），铁响应元件（29 nt），炭疽杆菌的氟化物核糖开关（48 nt），以及来自人类日冕病毒（59 nt）的移码元件。最后，我们展示了由于拥挤减少和线宽变窄而引起的频谱质量的改善，以及对NMR弛豫色散（CPMG）和基于TROSY的CEST实验的精确分析，以测量μs-ms时标运动，以及改进的NOESY共振分配策略。这种选择性标记技术的应用有望减少与化学位移重叠和信号快速衰减相关的困难，这使得研究PDB中超过50 nt中值大小的大RNA的结构和动力学变得具有挑战性。
• An efficient synthesis of [8-13C]adenine
  作者：William H. Gmeiner、C. Dale Poulter

  DOI：10.1021/jo00241a041

  日期：1988.3
• Synthesis and Utilization of¹³C(8)-Enriched Purines
  作者：Christopher J. Lafrancois、June Fujimoto、Lawrence C. Sowers

  DOI：10.1080/07328319908045591

  日期：1999.1

  A new and more efficient method is presented for the synthesis of 13C(8)-enriched adenine. In addition, we present for the first time the synthesis of 13C(8)-enriched 2-aminopurine and purine. All three analogues have been converted to the corresponding ribonucleosides. The adenine analogue has been further converted to the 2'-deoxy-nucleoside and incorporated into a synthetic oligonucleotide. Data is presented demonstrating the utility of 13C-enrichment in heteronuclear isotope-edited NMR spectra.