(-)-N⁶-(1-pyrenylmethyl)-2'-deoxyadenosine | 132183-36-9

• 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: (-)-N⁶-(1-pyrenylmethyl)-2'-deoxyadenosine
• 英文别名: 2'-deoxy-N⁶-(1-pyrenylmethyl)adenosine；2'-deoxy-N⁶-(pyren-1-ylmethy)adenosine；(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(pyren-1-ylmethylamino)purin-9-yl]oxolan-3-ol
• CAS: 132183-36-9
• 化学式: C₂₇H₂₃N₅O₃
• 分子量: 465.511
• InChiKey: RPLXSXBLRHTGKK-BHDDXSALSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  809.2±75.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-N⁶-(1-pyrenylmethyl)-2'-deoxyadenosine 生成 (+/-)-N⁶-(1-Pyrenylmethyl)-2'-deoxy-3'-(N,N-diisopropyl-2-cyanoethyl)-5'-(p-dimethoxytrityl)adenosine phosphoramidite
  参考文献：
  名称：

  在脱氧鸟苷和脱氧腺苷的氨基官能团上烷基化的多环芳香烃核苷酸和寡核苷酸加合物的合成

  摘要：

  描述了具有连接至脱氧鸟苷和脱氧腺苷的环外氨基官能团的烃部分的1-苯甲基甲基单核苷加合物的有效合成。

  DOI：

  10.1016/s0040-4039(00)97168-5
• 作为产物：
  描述：

  2'-脱氧腺苷 在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 8.0h， 生成 (-)-N⁶-(1-pyrenylmethyl)-2'-deoxyadenosine
  参考文献：
  名称：

  1H-苯并三唑作为合成辅助剂在 N6-(芳甲基)-2'-脱氧腺苷的简便途径中：插入三向连接的 DNA 嵌入剂

  摘要：

  The 2'-deoxy-N-6-(naphthalen-1-ylmethyl)-(5a) and N-6-(pyren-1-ylntethyl)adenosine (5b) were synthesized in two steps from 2'-deoxyadenosine and the adequate arenecarbaldehyde with 1H-benzotriazole as a synthetic auxiliary (Scheme). When the N-6-(arylmethyl)-2'-deoxyadenosines were inserted into the junction region of a DNA three-way junction, its thermal stability increased.

  DOI：

  10.1002/1522-2675(20000705)83:7<1408::aid-hlca1408>3.0.co;2-u

文献信息

• A Highly Facile and Efficient One-Step Synthesis of <i>N</i>⁶-Adenosine and <i>N</i>⁶-2‘-Deoxyadenosine Derivatives
  作者：Zhao-Kui Wan、Eva Binnun、Douglas P. Wilson、Jinbo Lee

  DOI：10.1021/ol052424+

  日期：2005.12.1

  [reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic

  [反应：见正文]已开发出一种高度容易和高效的一步合成N6-腺苷和N6-2'-脱氧腺苷衍生物的方法。在DMF中存在BOP和DIPEA的情况下，在没有烷基糖基或芳基胺的情况下用烷基或芳基胺处理肌苷或2'-脱氧肌苷，导致形成N6-腺苷和N6-2'-脱氧腺苷衍生物，优异的产量。因此，由2'-脱氧肌苷直接以98％的产率直接合成了致癌的多环芳烃（PAH）N6-2'-脱氧腺苷加合物10和稀有DNA成分11。
• Syntheses of polycyclic aromatic hydrocarbon-nucleoslde and oligonucleotide adducts specifically alkylated on the amino functions of deoxyguanosine and deoxyadenosine
  作者：Hongmee Lee、Michael Hinz、John J. Stezowski、Ronald G. Harvey

  DOI：10.1016/s0040-4039(00)97168-5

  日期：1990.1

  Efficient syntheses of 1-pyrenylmethyl-mononucleoside adducts with the hydrocarbon moiety attached to the exocyclic amino functions of deoxyguanosine and deoxyadenosine are described.

  描述了具有连接至脱氧鸟苷和脱氧腺苷的环外氨基官能团的烃部分的1-苯甲基甲基单核苷加合物的有效合成。
• Synthesis of Oligonucleotide Adducts of the Bay Region Diol Epoxide Metabolites of Carcinogenic Polycyclic Aromatic Hydrocarbons
  作者：Hongmee Lee、Ernestina Luna、Michael Hinz、John J. Stezowski、Alexander S. Kiselyo、Ronald G. Harvey

  DOI：10.1021/jo00122a048

  日期：1995.9

  An efficient method for the site-specific synthesis of adducts between the biologically active diol epoxide metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAHs) and oligonucleotides in which a PAH component of predetermined stereochemistry is linked covalently to the exocyclic amino groups of deoxyadenosine (dA) and deoxyguanosine (dG) is described. The synthetic strategy involves in the key step coupling a protected halopurine derivative with an amino derivative (or an aminotriol derivative) of the PAH. This method was initially employed to prepare the dA and dG adducts of the model PAH 1-methylpyrene. The appropriately protected dA adduct was then incorporated into the oligonucleotide sequence d(GCAGGTCA(*)AGAG) where A(*) represents N6-pyrenylmethyl-dA. This methodology was extended to the synthesis of trans adducts of anti-diol epoxide metabolites of benzo[a]pyrene and 5-methylchrysene linked to the 6-amino function of dA. The parent hydrocarbons are widespread environmental carcinogens. This synthetic approach, dubbed the total synthesis method, complements the direct synthesis method which involves the direct reaction of PAH diol epoxides with oligonucleotides. The total synthesis method is broader in scope than the latter, and it is readily adaptable to the large scale preparation of PAH-oligonucleotide adducts required for structure determination by high resolution NMR and X-ray crystallographic techniques.
• A Rapid, High-Yield Method for 5′-Hydroxyl Protection in Very Reactive and Amino Group Modified Nucleosides Using Dimethoxytrityl Tetrafluoroborate
  作者：Mahesh K. Lakshman、Barbara Zajc

  DOI：10.1080/07328319608002032

  日期：1996.5

  The conventional method for 4,4'-dimethoxytrityl (DMT) etherification of the 5'-hydroxyl termini in deoxynucleosides that are either highly reactive or those bearing modifications at the exocyclic amino group can be quite problematic, and in several cases the yields are at best mediocre. Herein, we report a rapid, convenient and general procedure for the facile 5'-hydroxyl protection of these nucleosides in exceptionally high yields using DM(+)BF(4)(.). This reagent is particularly useful for the preparation of 5'-O-DMT ethers of nucleosides that are either synthetically valuable or for those that undergo degradation under standard conditions.
• LEE, HONGMEE;HINZ, MICHAEL;STEZOWSKI, JOHN J.;HARVEY, RONALD G., TETRAHEDRON LETT., 31,(1990) N7, C. 6773-6776
  作者：LEE, HONGMEE、HINZ, MICHAEL、STEZOWSKI, JOHN J.、HARVEY, RONALD G.

  DOI：——

  日期：——