2'-deoxyadenylyl(3'-5')-2'-deoxyadenosine | 23339-45-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 2'-deoxyadenylyl(3'-5')-2'-deoxyadenosine
• 英文别名: 2'-deoxy-adenylyl-(5'->3')-2'-deoxy-adenosine；2'-Deoxyadenylyl-(3'-5')-2'-deoxyadenosine；[(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 23339-45-9
• 化学式: C₂₀H₂₅N₁₀O₈P
• 分子量: 564.454
• InChiKey: VYQONXIMMXHHKS-PRSXHHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  254
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2-(5-氯羰基-2-唑基)-5,6-亚甲基二羟基苯并呋喃 、 2'-deoxyadenylyl(3'-5')-2'-deoxyadenosine 在 吡啶 、 sodium azide 作用下， 以 苯 为溶剂， 反应 24.0h， 以14%的产率得到(2-Furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-6-yl-oxazol-5-yl)-carbamic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-{[(2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Precolumn Derivatization of Nucleotides Based on Fluorescent Carbamate Formation on the Sugar Moieties in High-Performance Liquid Chromatography.

  摘要：

  描述了核苷酸与2-(5-氯碳酰基-2-噁唑基)5,6-亚甲基二氧苯并呋喃在存在叠氮化钠的条件下进行荧光衍生化，并通过高效液相色谱分离衍生物。该试剂与核苷酸的5'末端羟基反应，生成相应的荧光氨基甲酸酯。单核苷酸和寡核苷酸的衍生物通过反相色谱柱（TSKgel ODS-80TM）分离，而八核苷酸和十核苷酸的衍生物则在尺寸排阻柱（TSKgel G3000SWXL）上分离。检测限（信噪比3）为0.8-6.0 pmol。在碱性磷酸酶介导的脱磷酸化后，5'-磷酸化核苷酸也会生成荧光衍生物。

  DOI：

  10.1248/cpb.40.2559
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 sodium hydroxide 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 生成 2'-deoxyadenylyl(3'-5')-2'-deoxyadenosine
  参考文献：
  名称：

  Facile nucleoside phoshorylation via hydroxyl activation

  摘要：

  DOI：

  10.1016/s0040-4039(00)86393-5

文献信息

• Synthesis of oligonucleotides via phosphoramidite approach utilizing 2-diphenylmethylsilylethyl (DPSE) as a phosphorus protecting group
  作者：Vasulinga T. Ravikumar、Tadeusz K. Wyrzykiewicz、Douglas L. Cole

  DOI：10.1016/s0040-4020(01)85503-4

  日期：——

  2-Diphenylmethylsilylethyl (DPSE) is a new protecting group for internucleotidic bonds in the synthesis of oligodeoxyribo nucleotides by the phosphoramidite approach. This group is stable to acidic conditions and can be removed under mild β-fragmentation conditions using aqueous ammonium hydroxide.

  2-二苯基甲基甲硅烷基乙基（DPSE）是通过亚磷酰胺方法合成寡脱氧核糖核苷酸中核苷酸间键的新保护基。该基团在酸性条件下稳定，可以在温和的β片段化条件下使用氢氧化铵水溶液除去。
• Hydrolysis of phosphomonoesters in nucleotides by cerium(IV) ions. Highly selective hydrolysis of monoester over diester in concentrated buffers
  作者：Sachiko Miyama、Hiroyuki Asanuma、Makoto Komiyama

  DOI：10.1039/a701481c

  日期：——

  Phosphomonoesters in nucleotides are efficiently hydrolysed by CeIV ions under physiological conditions. The half-lives of the residues at pH 7.2 and 50 °C ([CeIV] = 10 mM) are around 10 min. Phosphomonoester hydrolysis by CeIV ions is faster than the hydrolysis of phosphodiesters. Significantly, the selectivity for monoester hydrolysis over diester hydrolysis is remarkably increased by using concentrated buffer solutions (TRIS and HEPES). In 500 mM TRIS buffer, pdA and dAp are hydrolysed 500- and 580-fold faster than is d(ApA), whereas the corresponding ratios in 50 mM TRIS buffer are 85 and 90 respectively. Selective removal of the terminal monophosphate from d(pApA) is achieved by CeIV in these concentrated buffers.

  在生理条件下，核苷酸中的磷酸单酯可被 CeIV 离子有效水解。在 pH 值为 7.2、温度为 50 °C 的条件下（[CeIV] = 10 mM），残基的半衰期约为 10 分钟。CeIV 离子水解磷酸单酯的速度快于水解磷酸二酯的速度。值得注意的是，使用浓缩缓冲溶液（TRIS 和 HEPES）可显著提高单酯水解对二酯水解的选择性。在 500 mM TRIS 缓冲溶液中，pdA 和 dAp 的水解速度分别是 d(ApA) 的 500 倍和 580 倍，而在 50 mM TRIS 缓冲溶液中的相应比率分别为 85 倍和 90 倍。在这些浓缩缓冲液中，CeIV 可以选择性地去除 d(pApA)的末端单磷酸。
• Synthesis of Oligo(Deoxyribonucleoside Phosphorodithioate)s by the Dithiaphospholane Approach
  作者：Andrzej Okruszek、Agnieszka Sierzcha-la、Karen L. Fearon、Wojciech J. Stec

  DOI：10.1021/jo00126a060

  日期：1995.10

  A novel method of synthesis of oligo(deoxyribonucleoside phosphorodithioate)s (S-2-ODNs), based on the ring-opening condensation of nucleoside 3'-0-(2-thiono-1,3,2-dithiaphospholane)s with 5'-O-deprotected nucleosi(ti)des in the presence of a strong organic base such as DBU, is presented. The process has been adapted to the requirements of automated solid-phase oligonucleotide synthesis with a relatively short condensation step (5 min) and reasonable step-yield(>95%). N-Methylpyrrolidin-2-ylidenyl (Pya) was found to be the group of choice for the protection of reactive aminofunctions of nucleobases in nucleotide substrates. Sarcosine-containing linker (LCA CPG SAR) was employed due to its known resistance to cleavage by DBU. Several medium-size S-2-ODNs were prepared by this approach. Their identity and purity was confirmed by means of P-31 NMR, gel electrophoresis, and mass spectrometry. It has been demonstrated that, contrary to a recent report, S-2-ODNs are not degraded by DNaseI.
• 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.
• DIKSHIT, ARCHANA;CHADDHA, MANJULA;SINGH, R. K.;MISRA, KRISHNA, CAN. J. CHEM., 66,(1988) N2, C. 2989-2994
  作者：DIKSHIT, ARCHANA、CHADDHA, MANJULA、SINGH, R. K.、MISRA, KRISHNA

  DOI：——

  日期：——