1-[3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purin-7-yl]-1-hexanol | 276681-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-[3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purin-7-yl]-1-hexanol
• 英文别名: 1,N6-Hydroxy-epoxyoctenal-deoxyadenosine；(2R,3S,5R)-5-[7-(1-hydroxyhexyl)imidazo[2,1-f]purin-3-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 276681-46-0
• 化学式: C₁₈H₂₅N₅O₄
• 分子量: 375.428
• InChiKey: FEGOOVAFKWZCFO-FGDMXMHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  118
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purin-7-yl]-1-hexanol 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 1-[3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]-purin-7-yl]-1-hexyl-2-methylpropanoate
  参考文献：
  名称：

  Site-specific incorporation of the 1-hexanol-1,N6-etheno-2′-deoxyadenosine adduct into oligodeoxyribonucleotides

  摘要：

  Modified oligonucleotides that contain the hydrophobic 1-hexanol-1,N-6-etheno-2'-deoxyadenosine adduct have been synthesized using a mild solid phase phosphoramidite chemistry. The presence and the integrity of the modified nucleoside in the synthetic oligomers were confirmed by electrospray ionization and MALDI mass spectrometry measurements together with analysis of the complete enzymatic hydrolysate by high performance liquid chromatography coupled to UV and fluorescent detection techniques. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00125-1
• 作为产物：
  描述：

  反-2-辛烯醛 在 碳酸氢钠 Oxone 、 1,1,1-三氟丙酮 、 sodium phosphate buffer 、 edetate disodium 作用下， 以 水 、 乙腈 为溶剂， 反应 123.0h， 生成 1-[3-(2-deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purin-7-yl]-1-hexanol
  参考文献：
  名称：

  Site-specific incorporation of the 1-hexanol-1,N6-etheno-2′-deoxyadenosine adduct into oligodeoxyribonucleotides

  摘要：

  Modified oligonucleotides that contain the hydrophobic 1-hexanol-1,N-6-etheno-2'-deoxyadenosine adduct have been synthesized using a mild solid phase phosphoramidite chemistry. The presence and the integrity of the modified nucleoside in the synthetic oligomers were confirmed by electrospray ionization and MALDI mass spectrometry measurements together with analysis of the complete enzymatic hydrolysate by high performance liquid chromatography coupled to UV and fluorescent detection techniques. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00125-1

文献信息

• Novel 1,<i>N</i>⁶-Etheno-2‘-deoxyadenosine Adducts from Lipid Peroxidation Products
  作者：Valdemir M. Carvalho、Flavio Asahara、Paolo Di Mascio、Ivan P. de Arruda Campos、Jean Cadet、Marisa H. G. Medeiros

  DOI：10.1021/tx9901682

  日期：2000.5.1

  the reaction of DDE with 2'-deoxyadenosine (dAdo) was investigated in an effort to assess its possible DNA damage potential. Besides 1,N(6)-etheno-2'-deoxyadenosine and two products, namely, 1-[3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-imidazo[2, 1-i]purin-7-yl]-1,2,3-octanetriol (adduct I) and 1-[3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3H-imidazo[2, 1-i]purin-7-yl]-1,2-heptanediol (adduct II)

  反式，反式-2,4-癸二醛（DDE）是一种广泛存在的α，β-不饱和醛，例如存在于食品，水和环境污染物中。DDE也是内源性产生的，是细胞膜中脂质过氧化作用的分解产物。在此处介绍的工作中，研究了DDE与2'-脱氧腺苷（dAdo）的反应，以评估其可能的DNA损伤潜力。除了1，N（6）-etheno-2'-脱氧腺苷和两个产品，即1- [3-（2-deoxy-beta-D-erythro-pentofuranosyl）-3H-咪唑并[2,1-i]嘌呤-7-基] -1,1,2,3-辛三醇（加合物I）和1- [3-（2-脱氧-β-D-赤-五呋喃糖基）-3H-咪唑并[2，1-i]嘌呤-7我们小组先前描述的[-yl] -1,2-庚二醇（加合物II），鉴定出两个新的乙炔加合物。因此，1- [3-（2-脱氧-β-D-赤-五呋喃糖基）-3H-咪唑并[2，1-i]嘌呤-7-基] -1-己醇（加合物III）和1- [
• Identification of Octenal-Related dA and dC Adducts Formed by Reactions with a Hemin-ω-6-fat Peroxidation Model System
  作者：Kazuaki Kawai、Yuya Kawasaki、Yumiko Kubota、Tomoyuki Kimura、Ryuichi Sawa、Tomonari Matsuda、Hiroshi Kasai

  DOI：10.1021/tx400245a

  日期：2013.10.21

  Deoxynucleosides were reacted in a lipid peroxidation model system, emulsified hemin-ethyl linoleate, and the adducts thus produced were analyzed by HPLC. Substantial amounts of stable adducts were detected in the dA- and dC-reaction mixtures. The structures of the major dA and dC adducts, other than the known 4-oxo-2-nonenal adducts, were determined to be etheno-type adducts, with a C-6 side chain bearing an a-hydroxyl-group. These results suggested that the substance involved in adduct formation is 2,3-epoxyoctanal. This compound showed mutagenicity in Salmonella strains TA 100 and TA 104 without the S-9 mix. In addition, based on the structure of a minor dC adduct, another possibly involved mutagen, 4-oxo-2-octenal, was proposed. These mutagens may be formed during storage and cooking of food, or during digestion, and may be involved in human cancers.