8,5(S)-环-2-脱氧腺苷酸 | 117182-88-4

• 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: 8,5(S)-环-2-脱氧腺苷酸
• 英文名称: (5'S)-5',8-cyclo-2'-deoxyadenosine
• 英文别名: 5',8-cyclo-2'-deoxyadenosine；(5'S)-cdA；(5'S)cdA；cdA；2'-Deoxy-8,5'-cycloadenosine；(1R,11S,12S,13S)-7-amino-15-oxa-2,4,6,9-tetrazatetracyclo[10.2.1.02,10.03,8]pentadeca-3,5,7,9-tetraene-11,13-diol
• CAS: 117182-88-4
• 化学式: C₁₀H₁₁N₅O₃
• 分子量: 249.229
• InChiKey: MBVGIEDXZGVICG-HPQVQDLLSA-N

物化性质

• 沸点：
  721.2±60.0 °C(Predicted)
• 密度：
  2.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8,5(S)-环-2-脱氧腺苷酸 在 水 作用下， 反应 35.0h， 生成 (5'R)-5',8-cyclo-2'-deoxyadenosine
  参考文献：
  名称：

  Solar one-way photoisomerisation of 5′,8-cyclo-2′-deoxyadenosine

  摘要：

  在阳光照射下，(5-S)-5-,8-环-2-脱氧腺苷2光异构化为(5-R)异构体1，这是当这些环嘌呤损伤在DNA中形成时更容易修复的损伤。

  DOI：

  10.1039/b718222h
• 作为产物：
  描述：

  8-溴-2'-脱氧腺苷 以 水 为溶剂， 反应 12.0h， 以12%的产率得到(5'R)-5',8-cyclo-2'-deoxyadenosine
  参考文献：
  名称：

  Site-Specific Introduction of (5‘S)-5‘,8-Cyclo-2‘-deoxyadenosine into Oligodeoxyribonucleotides

  摘要：

  DOI：

  10.1021/jo980083q

文献信息

• Model Studies of DNA C5‘ Radicals. Selective Generation and Reactivity of 2‘-Deoxyadenosin-5‘-yl Radical
  作者：Chryssostomos Chatgilialoglu、Maurizio Guerra、Quinto G. Mulazzani

  DOI：10.1021/ja029374d

  日期：2003.4.1

  cyclization is 1.6 x 10(5) s(-1). On the basis of the theoretical findings, the cyclization step is highly stereospecific. The rate constants for the reactions of C5' and aminyl 3 radicals with different oxidants were determined by pulse radiolysis methods. The respective rate constants for the reaction of 2'-deoxyadenosin-5'-yl radical with dioxygen, Fe(CN)(6)(3)(-), and MV(2+) in water at ambient temperature

  水合电子 (e(aq)(-)) 与 8-bromo-2'-deoxyadenosine 的反应已通过辐射分解方法与产品研究相结合进行了研究，并通过 DFT-B3LYP 计算解决了计算问题。脉冲辐解显示该反应在大约 0.3 亩内完成，此时未检测到显着吸收。在 20 亩内形成的瞬态光谱在 300-500 nm 范围内具有吸光度（epsilon(max) 与 360 nm 处的 9600 M(-1) cm(-1) 一致），并且它被指定为芳香胺基3. 计算出的垂直跃迁 (TD-UB3LYP/6-311+G) 与实验观察非常吻合。自由基 3 通过以下反应序列获得：C-Br 键的单电子还原裂解产生 C8 自由基，从 C8 到 C5' 的快速自由基易位 位置，以及 C5' 基团在腺嘌呤部分的 C8,N7 双键上的分子内攻击。环化的速率常数为 1.6 x 10(5) s(-1)。根据理论发现，环化步骤具有
• C5‘-Adenosinyl Radical Cyclization. A Stereochemical Investigation
  作者：Maria Luisa Navacchia、Chryssostomos Chatgilialoglu、Pier Carlo Montevecchi

  DOI：10.1021/jo060197z

  日期：2006.6.1

  A variety of substituted 2'-deoxyadenosin-5'-yl radicals 3 were generated under different reaction conditions. Radicals 3 underwent intramolecular cyclization onto the C8-N7 double bond of the adenine moiety leading to aminyl radicals (5'S,8R)-4 and (5'R,8R)-4 and, eventually, to the corresponding cyclonucleosides 5 and 6. The effect of the solvent, the nature of the substituents, and the generation method of radicals 3 on the stereoselectivity of the C5'-radical cyclization have been considered. The observed increase of the (5'S)/(5'R) ratio by increasing the bulkiness of the R-1 group is explained in terms of steric repulsion between R-1 and the purine moiety which favors the C5'-endo conformation, whereas the effect of the water solvent in promoting the (5'R)-stereoselective cyclization is ascribed to intermolecular hydrogen bonding stabilizing the C5'-exo confomation.
• Oxidative damage to DNA constituents by iron-mediated Fenton reactions: the deoxyadenosine family
  作者：Rajagopal Chattopadhyaya、Bhaswati Goswami

  DOI：10.1080/07391102.2012.682206

  日期：2012.8.1

  The effect of exposing 2'-deoxyadenosine (dA), 5'-dAMP, 3'-dAMP, dApA, dA(pdA)(19), and poly(dA): oligo(dT) to iron/H2O2 in the presence and absence of ethanol or NADH has been studied. HPLC retention times, enzyme treatments, radiolabeled substrates, UV absorption spectra, and fast atom bombardment mass spectrometry (FABMS) have been used to distinguish 20 products arising from the reaction, of which 16 have been identified and four anomers proposed by comparison with earlier gamma radiation studies. The radical responsible for the reactions seems to be analogous to radiation-derived (OH)-O-center dot, has many products in common, but has some novel ones probably specific for Fenton-induced damage. Two new dimeric adducts arising from the generation of hydroxylamine at N7 and its subsequent condensation with two known sugar damage products, dR-adenine-N1-oxide, and two isomers of dR-FAPy arising from radical attacks at C4 and C5, may be considered novel in the present study. Unlike radiation-derived (OH)-O-center dot, the radical under study is difficult to eliminate due to its generation in the proximity of the substrate molecules. It is proposed that the iron binds to the phosphate group and generates the radical in its vicinity. Strand breaks in dA(pdA)(11) resulting from the Fenton reaction are of two types, spontaneous and alkali-labile. Duplex DNA is less sensitive to attack by this radical, as its various degradation products are a subset of those obtained with monomer substrates and only dR-FAPy production is relatively enhanced for poly (dA): oligo (dT) as compared to those from other substrates.
• Site-Specific Introduction of (5‘<i>S</i>)-5‘,8-Cyclo-2‘-deoxyadenosine into Oligodeoxyribonucleotides
  作者：Anthony Romieu、Didier Gasparutto、Didier Molko、Jean Cadet

  DOI：10.1021/jo980083q

  日期：1998.7.1
• Solar one-way photoisomerisation of 5′,8-cyclo-2′-deoxyadenosine
  作者：Liliana B. Jimenez、Susana Encinas、Chryssostomos Chatgilialoglu、Miguel A. Miranda

  DOI：10.1039/b718222h

  日期：——

  Under sunlight irradiation (5′S)-5′,8-cyclo-2′-deoxyadenosine 2 photoisomerises to the (5′R) isomer 1, which is the more easily repaired damage when these cyclopurine lesions are formed in DNA.

  在阳光照射下，(5-S)-5-,8-环-2-脱氧腺苷2光异构化为(5-R)异构体1，这是当这些环嘌呤损伤在DNA中形成时更容易修复的损伤。