(2R,3R)-2'-deoxy-N²-(2,3,4-trihydroxybut-1-yl)guanosine

• 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: (2R,3R)-2'-deoxy-N²-(2,3,4-trihydroxybut-1-yl)guanosine
• 英文别名: 9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-[[(2R,3R)-2,3,4-trihydroxybutyl]amino]-1H-purin-6-one
• 化学式: C₁₄H₂₁N₅O₇
• 分子量: 371.35
• InChiKey: BNTRJLZBUZUUNY-VAPHQMJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  182
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2R,3R)-1-amino-2,3,4-butanetriol 、 (2R,3S,5R)-5-[2-氟-6-(2-三甲基硅烷基乙氧基)嘌呤-9-基]-2-(羟基甲基)四氢呋喃-3-醇 在 N,N-二异丙基乙胺 、 溶剂黄146 作用下， 以 二甲基亚砜 、 水 为溶剂， 反应 22.0h， 生成 (2R,3R)-2'-deoxy-N²-(2,3,4-trihydroxybut-1-yl)guanosine
  参考文献：
  名称：

  Synthesis and Characterization of Nucleosides and Oligonucleotides Bearing Adducts of Butadiene Epoxides on Adenine N⁶ and Guanine N²

  摘要：

  Butadiene is a major industrial chemical whose genotoxic effects are attributed to the reaction of its oxidized metabolites, butadiene monoepoxide (BDO) and butadiene diepoxide (BDO2), with DNA, Nucleosides and oligonucleotides containing regio- and stereochemically specific adducts of BDO and the BDO2-related compound, butene 3,4-diol 1,2-epoxide (BDE), on guanine [(2R)- and (2S)-N-2-(1-hydroxy-3-buten-2-yl) and (2R,3R)- and (2S,3S)-N-2-(2,3,4-trihydroxybutl-yl), respectively] and on adenine [(2R)- and (2S)-N-6-(1-hydroxy-3-buten-2-yl) and (2R,3R)and (2S,3S)-N-6-(2,3,4-trihydroxybut-1-yl), respectively] have been prepared by nonbiomimetic routes, For guanine adducts, 2-fluoro-O-6-(trimethylsilylethyl)-2 ' -deox was treated with (2R)- and (2S)-2-amino-3-buten-1-ol to give the BDO adducts and with (2R,3R)- and (25,35)1-amino-2,3,4-butanetriol to produce the BDE adducts; the adducted oligonucleotides were prepared from 11-mer oligonucleotides containing the halopurine. Adenine adducts were prepared in a similar fashion using 6-chloropurine 2 ' -deoxyriboside as the reactive purine component.

  DOI：

  10.1021/tx000241k

文献信息

• Synthesis and Characterization of Nucleosides and Oligonucleotides Bearing Adducts of Butadiene Epoxides on Adenine N⁶ and Guanine N²
  作者：Lubomir V. Nechev、Mingzhu Zhang、Dimitrios Tsarouhtsis、Pamela J. Tamura、Amanda S. Wilkinson、Constance M. Harris、Thomas M. Harris

  DOI：10.1021/tx000241k

  日期：2001.4.1

  Butadiene is a major industrial chemical whose genotoxic effects are attributed to the reaction of its oxidized metabolites, butadiene monoepoxide (BDO) and butadiene diepoxide (BDO2), with DNA, Nucleosides and oligonucleotides containing regio- and stereochemically specific adducts of BDO and the BDO2-related compound, butene 3,4-diol 1,2-epoxide (BDE), on guanine [(2R)- and (2S)-N-2-(1-hydroxy-3-buten-2-yl) and (2R,3R)- and (2S,3S)-N-2-(2,3,4-trihydroxybutl-yl), respectively] and on adenine [(2R)- and (2S)-N-6-(1-hydroxy-3-buten-2-yl) and (2R,3R)and (2S,3S)-N-6-(2,3,4-trihydroxybut-1-yl), respectively] have been prepared by nonbiomimetic routes, For guanine adducts, 2-fluoro-O-6-(trimethylsilylethyl)-2 ' -deox was treated with (2R)- and (2S)-2-amino-3-buten-1-ol to give the BDO adducts and with (2R,3R)- and (25,35)1-amino-2,3,4-butanetriol to produce the BDE adducts; the adducted oligonucleotides were prepared from 11-mer oligonucleotides containing the halopurine. Adenine adducts were prepared in a similar fashion using 6-chloropurine 2 ' -deoxyriboside as the reactive purine component.