1-(2,4-dideoxy-D-ribityl)thymine | 139973-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2,4-dideoxy-D-ribityl)thymine
• 英文别名: 1-[(3S)-3,5-dihydroxypentyl]-5-methyl-pyrimidine-2,4-dione；1-[(3S)-3,5-dihydroxypentyl]-5-methylpyrimidine-2,4-dione
• CAS: 139973-29-8
• 化学式: C₁₀H₁₆N₂O₄
• 分子量: 228.248
• InChiKey: YEPCFTBHKDVDKM-QMMMGPOBSA-N

物化性质

• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,4-dideoxy-D-ribityl)thymine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 Diisopropyl-phosphoramidic acid (S)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl]-propyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Acyclic oligonucleotides: possibilities and limitations

  摘要：

  Oligonucleotides containing acyclic nucleosides with a 3(S),5-dihydroxypentyl (1a-e) or 4(R)-methoxy-3(S),5-dihydroxypentyl (2a) side chain were prepared and their hybridization properties as well as their stability towards degradation with snake venom posphodiesterase were studied. Attachment of an acyclic nucleoside at the 3'-end of an oligonucleotide makes it extremely resistant against enzymatic breakdown. Whereas oligonucleotides consisting completely of acyclic 2'-deoxyadenosine analogues (1a or 2a) can still hybridize with an unmodified oligothymidylate, completely modified oligothymidylates or hetero-oligomers do not hybridize with their unmodified complementary oligonucleotide. This can be explained by the favourable enthalpy change on hybridization for the oligomers with adenine bases because of their higher degree of stacking and the ability to form T-A . T triplets. In base-pairing with the natural DNA-nucleosides (dA,dC,dG,T), the acyclic nucleoside analogues (1a-e) discriminate less compared to the natural 2'-deoxynucleosides. 9-(3(S),5-Dihydroxypentyl)hypoxanthine shows the least spreading in melting temperature on hybridization with the four natural 2'-deoxynucleosides. Because of their conformation flexibility, acyclic nucleosides can be considered as universal nucleoside for the design of probes with ambiguous positions.

  DOI：

  10.1016/s0040-4020(01)87200-8
• 作为产物：
  描述：

  1-O-trityl-3,5-di-O-benzyl-2-deoxy-D-ribitol 在 palladium dihydroxide 咪唑 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 环己烯 为溶剂， 反应 53.5h， 生成 1-(2,4-dideoxy-D-ribityl)thymine
  参考文献：
  名称：

  具有3（S），5-二羟基戊基或4（R）-甲氧基-3（S），5-二羟基戊基侧链的无环核苷的合成及其抗病毒活性。

  摘要：

  从2-脱氧-D-核糖开始合成具有3（S），5-二羟基戊基或4（R）-甲氧基-3（S），5-二羟基戊基侧链的光学纯的无环核苷类似物。通过用甲磺酸酯16和17使碱基烷基化获得无环核苷。在这一系列新型核苷类似物中，只有9- [3（S），5-二羟基戊-1-基]鸟嘌呤（6d）显示出显着的抗病毒活性。它以0.4-0.6微克/毫升的浓度抑制1型单纯疱疹病毒（HSV-1）的细胞致病性，因此表明其抗病毒活性比最近报道的R和S对映异构体混合物（12.5微克/毫升）高。毫升）。与6d相反，其4（R）-甲氧基衍生物7d没有显示抗病毒活性，这意味着4'-甲氧基不能模仿正常呋喃糖环的1'，4'-氧桥。

  DOI：

  10.1021/jm00086a015

文献信息

• Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3(S),5-dihydroxypentyl sidechain
  作者：Frank Vandenriessche、Robert Snoeck、Gerard Janssen、Jos Hoogmartens、Arthur Van Aerschot、Erik De Clercq、Piet Herdewijn

  DOI：10.1021/jm00086a015

  日期：1992.4

  Optically pure acyclic nucleoside analogues with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3(S),5-dihydroxypentyl side chain were synthesized starting from 2-deoxy-D-ribose. The acyclic nucleosides were obtained by alkylation of the bases with the mesylates 16 and 17. Of these series of novel nucleoside analogues only 9-[3(S),5-dihydroxypent-1-yl]guanine (6d) showed marked antiviral activity. It inhibited the

  从2-脱氧-D-核糖开始合成具有3（S），5-二羟基戊基或4（R）-甲氧基-3（S），5-二羟基戊基侧链的光学纯的无环核苷类似物。通过用甲磺酸酯16和17使碱基烷基化获得无环核苷。在这一系列新型核苷类似物中，只有9- [3（S），5-二羟基戊-1-基]鸟嘌呤（6d）显示出显着的抗病毒活性。它以0.4-0.6微克/毫升的浓度抑制1型单纯疱疹病毒（HSV-1）的细胞致病性，因此表明其抗病毒活性比最近报道的R和S对映异构体混合物（12.5微克/毫升）高。毫升）。与6d相反，其4（R）-甲氧基衍生物7d没有显示抗病毒活性，这意味着4'-甲氧基不能模仿正常呋喃糖环的1'，4'-氧桥。
• Acyclic oligonucleotides: possibilities and limitations
  作者：Frank Vandendriessche、Koen Augustyns、Arthur Van Aerschot、Roger Busson、Jos Hoogmartens、Piet Herdewijn

  DOI：10.1016/s0040-4020(01)87200-8

  日期：1993.8

  Oligonucleotides containing acyclic nucleosides with a 3(S),5-dihydroxypentyl (1a-e) or 4(R)-methoxy-3(S),5-dihydroxypentyl (2a) side chain were prepared and their hybridization properties as well as their stability towards degradation with snake venom posphodiesterase were studied. Attachment of an acyclic nucleoside at the 3'-end of an oligonucleotide makes it extremely resistant against enzymatic breakdown. Whereas oligonucleotides consisting completely of acyclic 2'-deoxyadenosine analogues (1a or 2a) can still hybridize with an unmodified oligothymidylate, completely modified oligothymidylates or hetero-oligomers do not hybridize with their unmodified complementary oligonucleotide. This can be explained by the favourable enthalpy change on hybridization for the oligomers with adenine bases because of their higher degree of stacking and the ability to form T-A . T triplets. In base-pairing with the natural DNA-nucleosides (dA,dC,dG,T), the acyclic nucleoside analogues (1a-e) discriminate less compared to the natural 2'-deoxynucleosides. 9-(3(S),5-Dihydroxypentyl)hypoxanthine shows the least spreading in melting temperature on hybridization with the four natural 2'-deoxynucleosides. Because of their conformation flexibility, acyclic nucleosides can be considered as universal nucleoside for the design of probes with ambiguous positions.