8-bromo-2'-deoxyinosine | 916735-48-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-bromo-2'-deoxyinosine
• 英文别名: 8-bromo-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 916735-48-3
• 化学式: C₁₀H₁₁BrN₄O₄
• 分子量: 331.126
• InChiKey: YEJPQKDYOHHMHH-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-bromo-2'-deoxyinosine 在 potassium hexacyanoferrate(III) 、 叔丁醇 作用下， 以60%的产率得到9-[(2R,4S,5S)-5-(dihydroxymethyl)-4-hydroxyoxolan-2-yl]-1H-purin-6-one
  参考文献：
  名称：

  氧化条件下嘌呤核苷的 C5' 基团的命运

  摘要：

  在有氧条件下，影响嘌呤部分 C5' 自由基反应性的因素不仅在 DNA 中是未知的，在简单的核苷中也是未知的。5',8-环嘌呤损伤是在与氧反应之前对嘌呤部分进行快速 C5' 自由基攻击的结果。溶液中分子氧的存在抑制了 DNA 修饰中这些众所周知的损伤。在这里，我们阐明了三个嘌呤取代的 C5' 自由基（即 2'-脱氧腺苷-5'-基、2'-脱氧肌苷-5'-基和 2'-脱氧鸟苷-5'-基）在氧化条件下的化学反应使用伽马辐射与产品研究相结合。2'-Deoxyadenosin-5'-yl 和 2'-deoxyinosin-5'-yl 自由基是通过水合电子 (e(aq)(-)) 与 8-bromo-2' 的反应选择性产生的 -deoxyadenosine 和 8-bromo-2'-deoxyinosine，然后是从 C8 到 C5' 位置的快速自由基易位。用 Fe(CN)6(3-) 捕获这两个 C5' 自由基，得到相应的水合

  DOI：

  10.1021/ja800763j
• 作为产物：
  描述：

  8-溴-2'-脱氧腺苷 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 8-bromo-2'-deoxyinosine 、 8-溴次黄嘌呤
  参考文献：
  名称：

  水溶液中8-溴2'-脱氧肌苷和8-溴肌苷的化学辐射研究。

  摘要：

  水合电子（e（aq）（-））与8-bromo-2'-deoxyinosine（8）和8-bromoinosine（12）的反应已通过辐射解法与产物研究相结合进行了研究，并已通过计算方法解决BB1K-HMDFT计算。脉冲辐射分解表明，C-Br键的单电子还原性裂解产生C8自由基9或13，然后快速自由基转移至糖部分。C5'自由基的选择性生成发生在2'-脱氧核糖衍生物中，而在核糖类似物中，反应以相似的速率分配在C5'和C2'位置之间。两个C5'自由基均经历环化反应10-> 11和14-> 15，其速率常数分别为1.4 x 10（5）和1.3 x 10（4）s（-1）。还已经研究了自由基10和11的氧化还原性质。还开发了一种合成有用的光反应法，该方法可通过一锅法以高收率和非对映异构体比率（5'R）/（5'S）将8'转化为5'，8-环2'-脱氧肌苷。 4：1。将本结果与先前获得的8-溴腺嘌呤和8-溴鸟

  DOI：

  10.1002/chem.200600040

文献信息

• [EN] DITHIOLANE FUNCTIONALIZED NUCLEOSIDE AMIDITES AND SUPPORTS FOR STRONGER IMMOBILIZATION OF BIO-MOLECULES ON SOLID SURFACES<br/>[FR] AMIDITES NUCLÉOSIDIQUES FONCTIONNALISÉES PAR DES DITHIOLANES ET SUPPORTS POUR IMMOBILISATION BIOMOLÉCULAIRES PLUS FORTE SUR DES SURFACES SOLIDES
  申请人：CHEMGENES CORP

  公开号：WO2015061507A1

  公开（公告）日：2015-04-30

  This invention is related to nucleic acid chemistry and describes novel 1,2- dithiolane functionalized nucleoside phosphoramidites (1, Chart 1) and corresponding solid supports (2, Chart 1). In addition to these derivatives, 1,2- dithiolane moiety can also be functionalized to at the various positions of the nucleobase and sugar part as shown in Schemes 1 to 8. The nucleosides of our invention carry a primary hydroxyl for DMTr (4,4'-dimethoxytrityl) function for chain elongation. Furthermore, the phosphoramidite function is attached at the 3'- hydroxyl of the nucleoside. This allows oligonucleotide chain extension under standard DNA and RNA synthesis chemistry conditions and techniques, thus leading to high quality oligonucleotides. These derivatives are useful for introduction of reactive thiol groups either at 3'- or 5 '-end of the oligonucleotides on the solid supports such as gold, silver and quantum dots.

  这项发明涉及核酸化学，并描述了新颖的1,2-二硫杂环己烷功能化的核苷酸磷酸酯（1，图1）及相应的固相支持体（2，图1）。除了这些衍生物外，1,2-二硫杂环己烷基团还可以在核碱基和糖部分的不同位置进行功能化，如方案1至8所示。我们发明的核苷酸携带一个主要的羟基用于DMTr（4,4'-二甲氧基三苯基）功能以进行链延伸。此外，磷酸酯功能连接在核苷酸的3'-羟基上。这使得在标准的DNA和RNA合成化学条件和技术下进行寡核苷酸链的延伸，从而产生高质量的寡核苷酸。这些衍生物可用于在金、银和量子点等固相支持体上引入反应性硫醇基团，无论是在寡核苷酸的3'-端还是5'-端。
• Photoinduced changes in hydrogen bonding patterns of 8-thiopurine nucleobase analogues in a DNA strand
  作者：Kunihiko Morihiro、Tetsuya Kodama、Shohei Mori、Satoshi Obika

  DOI：10.1039/c3ob42427h

  日期：——

  Hydrogen bonds (H-bonds) formed between nucleobases play an important role in the construction of various nucleic acid structures. The H-donor and H-acceptor pattern of a nucleobase is responsible for selective and correct base pair formation. Herein, we describe an 8-thioadenine nucleobase analogue and an 8-thiohypoxanthine nucleobase analogue with a photolabile 6-nitroveratryl (NV) group on the sulfur

  核碱基之间形成的氢键（H键）在各种核酸结构的构建中起重要作用。核碱基的H-供体和H-受体模式负责选择性和正确的碱基对形成。在本文中，我们描述了在硫原子上分别具有光不稳定的6-硝基veratryl（NV）基团的8-thioadenine核碱基类似物和8-thiohypoxanthine核碱基类似物（分别为SA NV和SH NV）。轻触发去除NV基团会导致互变异构化，并改变SA NV和SH NV的H键结构。H键模式的这种变化对8-硫嘌呤核碱基类似物的碱基识别有很大的影响。特别地，SH NV的碱基识别在光辐照下明显从鸟嘌呤变为腺嘌呤。这些结果表明，H键模式的光诱导变化是利用时空控制操纵核酸组装的独特策略。
• Highly efficient synthesis of long RNA using reverse direction approach
  申请人：ChemGenes Corporation

  公开号：US10167308B2

  公开（公告）日：2019-01-01

  The present invention relates to novel process of reverse 5′→3′ directed synthesis of RNA oligomers in the range of about 100-mer to about 200-mer has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

  本发明涉及反向 5′→3′ 定向合成约 100-mer 至约 200-mer 范围内 RNA 寡聚体的新工艺。使用该方法可实现高质量的 RNA 合成，耦合效率接近 99%。
• Importance of the C2, N7, and C8 Positions to the Mutagenic Potential of 8-Oxo-2′-deoxyguanosine with Two A Family Polymerases
  作者：Michelle L. Hamm、Kelly A. Crowley、Michael Ghio、Laura Del Giorno、Margaret A. Gustafson、Kevin E. Kindler、Claire W. Ligon、Maria A. M. Lindell、Emily J. McFadden、Carlos Siekavizza-Robles、Matthew R. Summers

  DOI：10.1021/bi201383c

  日期：2011.12.13

  8-Oxo-2'-deoxyguanosine (OdG) is a prominent DNA lesion produced from the reaction of 2'-deoxyguanosine (dG) with reactive oxygen species. While dG directs the insertion of only dCTP during replication, OdG can direct the insertion of either dCTP or dATP, allowing for the production of dG -> dT transversions. When replicated by Klenow fragment-exo (KF-exo), OdG preferentially directs the incorporation of dCTP over dATP, thus decreasing its mutagenic potential. However, when replicated by a highly related polymerase, the large fragment of polymerase I from Bacillus stearothermophilus (BF), dATP incorporation is preferred, and a higher mutagenic potential results. To gain insight into the reasons for this opposite preference and the effects of the C2, N7, and C8 positions on OdG mutagenicity, single-nucleotide insertions of dCTP and/or dATP opposite dG, OdG, and seven of their analogues were examined by steady state kinetics with both KF-exo and BF. Results from these studies suggest that the two enzymes behave similarly and are both sensitive not only to steric and electronic changes within the imidazole ring during both dCTP and dATP incorporation but also to the presence of the C2-exocyclic amine during dATP incorporation. The difference in incorporation preference opposite OdG appears to be due to a somewhat increased sensitivity to structural perturbations during dCTP incorporation with BF. Single-nucleotide extensions past the resulting base pairs were also studied and were not only similar between the two enzymes but also consistent with published ternary crystallographic studies with BF. These results are analyzed in the context of previous biochemical and structural studies, as well as stability studies with the resulting base pairs.
• RNA SYNTHESIS - PHOSPHORAMIDITES FOR SYNTHETIC RNA IN THE REVERSE DIRECTION, AND APPLICATION IN CONVENIENT INTRODUCTION OF LIGANDS, CHROMOPHORES AND MODIFICATIONS OF SYNTHETIC RNA AT THE 3' - END
  申请人：Chemgenes Corporation

  公开号：EP2326656A2

  公开（公告）日：2011-06-01