9-(5-溴戊基)嘌呤-6-胺 | 81792-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-(5-溴戊基)嘌呤-6-胺
• 英文名称: 9-(5-bromopentyl)-adenine
• 英文别名: 9-(5-bromopentyl)adenine；9-(5-Bromopentyl)-9H-purin-6-amine；9-(5-bromopentyl)purin-6-amine
• CAS: 81792-13-4
• 化学式: C₁₀H₁₄BrN₅
• 分子量: 284.159
• InChiKey: DGOAQXCGAWUKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-(5-溴戊基)嘌呤-6-胺 在 Sodium thiosulfate pentahydrate 作用下， 以 水 为溶剂， 反应 2.5h， 以91%的产率得到S-(5-(6-amino-9H-purin-9-yl)pentyl) O-hydrogen sulfurothioate
  参考文献：
  名称：

  Self-Assembled Monolayers of Double-Chain Disulfides of Adenine on Au: An IR-UV Sum-Frequency Generation Spectroscopic Study

  摘要：

  We have synthesized double-chain disulfides of adenine with different chain lengths (n = 2,4, 5, 9, and 10) and studied their self-assembled monolayers (SAM) oil gold surface by IR-UV doubly resonant sum frequency generation spectroscopy with the help of DFT calculation. A versatile way to investigate the orientation angle of functional groups of SAMs and their surface coverage has been demonstrated, It was revealed that the I R dipoles of the band at around 1630 cm(-1), which were almost parallel to the long molecular axis of the adenine ring, were less tilted with respect to the substrate surface in the SAMs with longer chains (n = 9 and W) in comparison to those with shorter chains (n = 2, 4, and 5).

  DOI：

  10.1021/la9021992
• 作为产物：
  描述：

  1,5-二溴戊烷 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以34%的产率得到9-(5-溴戊基)嘌呤-6-胺
  参考文献：
  名称：

  NMR study of stacking interactions between adenine and xanthine rings

  摘要：

  比较了 7-[ω-(6-氨基嘌呤-9-基)烷基]-1,3-二甲基黄嘌呤（1）与 1-[ω-(6-氨基嘌呤-9-基)烷基]-3,7-二甲基黄嘌呤（2）在 pD 7.0、1.0 和 13.0 的缓冲溶液中以及在有机溶剂中的腺嘌呤环和黄嘌呤环质子的化学位移与其聚亚甲基链中碳原子数（n = 2-10）之间的关系。此外，还研究了浓度依赖性和温度对 1 和 2 化学位移的影响。在 pD 值为 7.0 和 13.0 的缓冲溶液中，1 和 2 的环质子的上场移位可以用腺嘌呤环和黄嘌呤环之间的堆叠相互作用来解释，而在 pD 值为 1.0 的缓冲溶液中的结果则可能是阳离子-π 相互作用所致。根据这些数据可以推测，堆积相互作用不仅包括腺嘌呤环和黄嘌呤环之间的相互作用。

  DOI：

  10.1039/a708866c

文献信息

• Molecular assemblies of bis- and tris-adenine derivatives
  作者：Toshio Itahara、Tomohide Uto、Miho Sunose、Takehiko Ueda

  DOI：10.1016/s0022-2860(02)00337-x

  日期：2002.10

  Abstract Molecular assemblies of bis- and tris-adenine derivatives were studied by means of NMR, IR, and DSC. Mixtures of the adenine derivatives and 1-hexadecylthymine showed multiple phase transitions in the temperature range of the solid phase. A difference of the NMR, IR, and DSC data between bis-adenine and tris-adenine derivatives may be attributable to a formation of intramolecular hydrogen

  摘要 利用NMR、IR和DSC研究了双腺嘌呤和三腺嘌呤衍生物的分子组装。腺嘌呤衍生物和 1-十六烷基胸腺嘧啶的混合物在固相温度范围内表现出多重相变。双腺嘌呤和三腺嘌呤衍生物之间 NMR、IR 和 DSC 数据的差异可能归因于分子内氢键的形成。
• New Porphyrin-Nucleobase Hybrid Compounds and Their Interaction with Nucleosides and Nucleic Acids
  作者：Vladimir Malinovski、Lydia Tumir、Ivo Piantanida、Mladen Zinic、Hans-Jörg Schneider

  DOI：10.1002/1099-0690(200211)2002:22<3785::aid-ejoc3785>3.0.co;2-4

  日期：2002.11

  described: one (1) with a methoxyphenyl group and three pyridinium units (for comparison only), and three others with either adenine (2, 3) or thymine (4) bases. The synthetic strategies vary from known literature procedures in that the methylation of pyridinium subunits takes place before the formation of the hybrid molecule, beginning with simultaneous condensation of pyridinealdehyde and 3-(propionyloxy)benzaldehyde

  描述了四种新的卟啉衍生物：一种 (1) 带有甲氧基苯基和三个吡啶鎓单元（仅供比较），另外三种带有腺嘌呤 (2, 3) 或胸腺嘧啶 (4) 碱基。合成策略不同于已知的文献程序，因为吡啶鎓亚基的甲基化发生在杂化分子形成之前，从吡啶醛和 3-(丙酰氧基)苯甲醛的同时缩合开始，随后在改进的条件下进行色谱。通过用合适的胸腺嘧啶-烷基溴处理，从三甲基化四吡啶基卟啉T4PyP获得胸腺嘧啶衍生物4。在水中的稀释实验表明在所使用的实验条件下不存在分子间卟啉缔合。UV 和 NMR 光谱数据表明卟啉部分和共价连接的核碱基之间存在强烈的分子内自堆积。这导致卟啉-核碱基缀合物对添加的核苷的亲和力比用参考化合物三-或四-吡啶鎓卟啉（分别为 1 和 TMPyP）观察到的更小。基于核碱基的互补性，化合物 2-4 没有显示出 A 和 T 之间的显着区分，这可以通过大量水与 Watson-Crick 氢键的强烈竞争来解释。配体
• Coumarin–nucleotide base pairs. Ultraviolet absorption, fluorescence, and photochemical study
  作者：Grażyna Wenska、Stefan Paszyc

  DOI：10.1139/v84-342

  日期：1984.10.1

  Bichromophoric compounds containing a nucleotide base and coumarin linked with a polymethylene chain have been synthesized. A hypochromic effect was observed for adenine–coumarin pairs in contrast to the thymine containing compound. The fluorescence intensity of coumarin when bound into these systems was found to be significantly reduced. It has also been demonstrated that excitation energy is transferred from adenine or thymine to the coumarin moiety. Intermolecular dimerization of coumarin residues was observed upon irradiation of an adenine–coumarin pair.

  已合成含有核苷酸碱基和香豆素的双色性化合物，它们通过聚亚甲基链连接。与含有胸腺嘧啶的化合物相比，腺嘌呤-香豆素对显示出次色效应。当香豆素结合到这些系统中时，其荧光强度明显降低。还表明，激发能从腺嘌呤或胸腺嘧啶转移至香豆素基团。在腺嘌呤-香豆素对辐射后观察到香豆素残基的分子间二聚化。
• Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives
  作者：Marijana Radić Stojković、Marko Škugor、Łukasz Dudek、Jarosław Grolik、Julita Eilmes、Ivo Piantanida

  DOI：10.3762/bjoc.10.225

  日期：——

  An investigation of the interactions of two novel and several known DBTAA–adenine conjugates with double-stranded DNA and RNA has revealed the DNA/RNA groove as the dominant binding site, which is in contrast to the majority of previously studied DBTAA analogues (DNA/RNA intercalators). Only DBTAA–propyladenine conjugates revealed the molecular recognition of AT-DNA by an ICD band pattern > 300 nm, whereas significant ICD bands did not appear for other ds-DNA/RNA. A structure–activity relation for the studied series of compounds showed that the essential structural features for the ICD recognition are a) the presence of DNA-binding appendages (adenine side chain and positively charged side chain) on both DBTAA side chains, and b) the presence of a short propyl linker, which does not support intramolecular aromatic stacking between DBTAA and adenine. The observed AT-DNA-ICD pattern differs from previously reported ss-DNA (poly dT) ICD recognition by a strong negative ICD band at 350 nm, which allows for the dynamic differentiation between ss-DNA (poly dT) and coupled ds-AT-DNA.

  对两种新型和多种已知的DBTAA-腺嘌呤共轭物与双链DNA和RNA的相互作用进行的研究表明，DNA/RNA沟槽是主要的结合位点，这与先前研究的大多数DBTAA类似物（DNA/RNA插入剂）不同。只有DBTAA-丙基腺嘌呤共轭物显示出AT-DNA的分子识别，通过ICD带模式> 300 nm，而其他ds-DNA/RNA没有出现显著的ICD带。所研究的化合物系列的结构活性关系表明，ICD识别的基本结构特征为a）DBTAA侧链上存在DNA结合附属物（腺嘌呤侧链和带正电的侧链），以及b）存在短的丙基连接器，它不支持DBTAA和腺嘌呤之间的分子内芳香堆积。观察到的AT-DNA-ICD模式与先前报道的ss-DNA（poly dT）ICD识别不同，后者在350 nm处具有强烈的负ICD带，允许动态区分ss-DNA（poly dT）和耦合的ds-AT-DNA。
• Highly Selective Ratiometric Fluorescence Determination of Ag⁺ Based on a Molecular Motif with One Pyrene and Two Adenine Moieties
  作者：Lei Liu、Deqing Zhang、Guanxin Zhang、Junfeng Xiang、Daoben Zhu

  DOI：10.1021/ol8006716

  日期：2008.6.5

  A highly selective ratiometric fluorescence sensor for Ag(+) was developed with a molecular motif containing one pyrene and two adenine moieties.