N6-羟基-2'-脱氧腺苷 | 51385-49-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N6-羟基-2'-脱氧腺苷
• 英文名称: N⁶-hydroxy-2'-deoxyadenosine
• 英文别名: N6-hydroxy-2'-deoxyadenosine；N⁶-hydroxy-2'-deoxy-adenosine；(2R,3S,5R)-5-[6-(hydroxyamino)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 51385-49-0
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: BFOWFSDEOHCFQL-RRKCRQDMSA-N

物化性质

• 沸点：
  741.0±70.0 °C(Predicted)
• 密度：
  1.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-bromo-9-[2-deoxy-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine 在 盐酸羟胺 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N6-羟基-2'-脱氧腺苷
  参考文献：
  名称：

  通过串联诺里斯I型光裂解，β片段的胺基自由基生成：2'-脱氧腺苷-N 6-基自由基的独立生成和反应性

  摘要：

  从嘌呤核苷中的氮氢键中提取出正式的氢原子，会产生对核酸氧化很重要的反应性中间体。本文中，我们描述了一种从2'-脱氧腺苷（dA•）的N 6-胺中提取氢原子而独立产生嘌呤自由基的方法。该方法涉及对酮（7b）进行顺序的Norrish I型光裂解，以及对最初形成的烷基（8b）进行β片段化以形成dA•和丙酮。DA•的形成随后激光闪光光解，这产生与λ的瞬时最大≈340纳米和更广泛的弱吸收在~560为中心。此瞬态以≥2×10 5 s –1的速度增长; 但是，计算和反应性数据表明，β片段的发生要快得多，这意味着在形成dA•时会消耗掉它。在亚铁离子或硫酚的存在下，7b的连续光解产生了良好的dA收率，而反应性较低的硫醇大概是由于极性不匹配而提供了较低的收率。通常，这种串联的光化学，β片段化方法有望用于核酸低聚物和/或聚合物中dA•的位点特异性生产，以及通常也可用于生产氨基自由基。

  DOI：

  10.1021/acs.joc.7b00093

文献信息

• Nucleosides and nucleotides. 111. Thermal stability of oligodeoxyribonucleotide duplexes containing N6-hydroxyadenine in substitution for adenine.
  作者：Hisayoshi NISHIO、Akira ONO、Akira MATSUDA、Tohru UEDA

  DOI：10.1248/cpb.40.1355

  日期：——

  An oligodeoxyribonucleotide containing N6-hydroxyadenine (H) has been synthesized. An order of Tms of duplexes consisting of 5'd'(CCTGGTAHCAGGTCC)3' : 5'd(GGACCTGNTACCAGG) (N = A, G, T, C) was H : T > H : G > H : A > H : C.

  已合成含有 N6-羟基腺嘌呤 (H) 的寡脱氧核糖核苷酸。由 5'd'(CCTGGTAHCAGGTCC)3' : 5'd(GGACCTGNTACCAGG) (N = A, G, T, C) 组成的双链体的 Tms 顺序为 H : T > H : G > H : A > H : C.
• 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.