8-methoxy-2'-deoxyguanosine | 96964-89-5

• 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-methoxy-2'-deoxyguanosine
• 英文别名: 8-Methoxydeoxyguanosine；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-methoxy-1H-purin-6-one
• CAS: 96964-89-5
• 化学式: C₁₁H₁₅N₅O₅
• 分子量: 297.271
• InChiKey: WNQRNUKAULNFLF-KVQBGUIXSA-N

物化性质

• 密度：
  1.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-methoxy-2'-deoxyguanosine 在 吡啶 、 苯硫酚 、 三乙胺 、 N,N-二异丙基乙胺 、 silver(l) oxide 、 肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (2R,3S,5R)-5-(2-benzamido-8-oxo-7,8-dihydro-9H-purin-9-yl)-2-((benzoyloxy)methyl)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine

  摘要：

  The nucleoside 2-amino-9-(2-deoxy-beta-D-ribofuranosyl)-7,8-dihydro-8-oxo-purine (dJ) was obtained in eight steps from 2'-deoxyguanosine. The appropriate protected phosphoramidite was synthesized and incorporated into DNA oligonucleotides. The thermal stability of heteroduplexes containing 2-amino-8-oxopurine (J) was investigated by UV-thermal denaturation experiments. The results obtained can be interpreted by the base pairing schemes involving the two edges of dJ depending on the anti and syn orientations. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.021
• 作为产物：
  描述：

  甲醇 、 8-溴-2'-脱氧鸟苷 在 sodium 作用下， 生成 8-methoxy-2'-deoxyguanosine
  参考文献：
  名称：

  8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells

  摘要：

  A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted-N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.

  DOI：

  10.1021/jm00147a012

文献信息

• Synthesis and Thermodynamic Stabilities of Damaged DNA Involving 8-Hydroxyguanine (7,8-Dihydro-8-Oxoguanine) in a<i>ras</i>-Gene Fragments
  作者：Shiro Koizume、Hiroyuki Kamiya、Hideo Inoue、Eiko Ohtsuka

  DOI：10.1080/15257779408012168

  日期：1994.7

  A new building block of 8-hydroxyguanine (7,8-dihydro-8-oxoguanine, oh(8)Gua) with a N-2-(N,N-dimethylaminomethylene) group was prepared for oligonucleotide synthesis. Oligodeoxyribonucleotides corresponding to a part of the human c-Ha-ras gene and containing oh(8)Gua in codon 12 were synthesized using the phosphoramidite monomer. The oligonucleotides were used for thermal denaturation studies and circular dichroism measurements. Thermodynamic parameters showed that, other than oh(8)Gua:C and oh(8)Gua:A pairs, oh(8)Gua at the first and second positions of codon 12 forms stable pairs with G and T, respectively. These results may explain the different spectra of mutations induced by the base at the first and second positions of codon 12.
• 8-Substituted guanosine and 2'-deoxyguanosine derivatives as potential inducers of the differentiation of Friend erythroleukemia cells
  作者：Tai Shun Lin、Jia Chong Cheng、Kimiko Ishiguro、Alan C. Sartorelli

  DOI：10.1021/jm00147a012

  日期：1985.9

  A variety of 8-substituted guanosine and 2'-deoxyguanosine derivatives were synthesized and tested as inducers of the differentiation of Friend murine erythroleukemia cells in culture. The most active agents in the guanosine series were 8-substituted-N(CH3)2, -NHCH3, -NH2, -OH, and -SO2CH3, which caused 68, 42, 34, 33, and 30% of erythroleukemia cells to attain benzidine positivity, a functional measure of maturation, at concentrations of 5, 1, 0.4, 5, and 5 mM, respectively. The 8-OH derivative of the 2'-deoxyguanosine series produced comparable activity, causing 62% benzidine-positive cells at a level of 0.2 mM. These findings indicate that 8-substituted analogues of guanosine and 2'-deoxyguanosine have the potential to terminate leukemia cell proliferation through conversion to end-stage differentiated cells.
• Synthesis and incorporation into DNA fragments of the artificial nucleobase, 2-amino-8-oxopurine
  作者：Claudio Cadena-Amaro、Muriel Delepierre、Sylvie Pochet

  DOI：10.1016/j.bmcl.2004.12.021

  日期：2005.2

  The nucleoside 2-amino-9-(2-deoxy-beta-D-ribofuranosyl)-7,8-dihydro-8-oxo-purine (dJ) was obtained in eight steps from 2'-deoxyguanosine. The appropriate protected phosphoramidite was synthesized and incorporated into DNA oligonucleotides. The thermal stability of heteroduplexes containing 2-amino-8-oxopurine (J) was investigated by UV-thermal denaturation experiments. The results obtained can be interpreted by the base pairing schemes involving the two edges of dJ depending on the anti and syn orientations. (C) 2004 Elsevier Ltd. All rights reserved.