4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one | 103173-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one
• 英文别名: 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-2H-pyrrolo[2,3-d]pyrimidin-2-one；7-deaza-2'-deoxyisoguanosine；4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo[2,3-d]pyrimidin-2-one；4-Amino-7-(2-deoxy-b-D-ribofuranosyl)-1,7-dihydro-2H-pyrrolo[2,3-d]pyrimidin-2-one；4-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrrolo[2,3-d]pyrimidin-2-one
• CAS: 103173-80-4
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: KRCGKJZLLPGTBU-XLPZGREQSA-N

物化性质

• 熔点：
  188-192 °C(Solv: ethanol (64-17-5))
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one 生成 Diphenyl-carbamic acid 4-(dibutylamino-methyleneamino)-7-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl ester
  参考文献：
  名称：

  Parallel-Stranded DNA Formed by New Base Pairs Related to the Isoguanine-Cytosine or Isocytosine-Guanine Motifs

  摘要：

  Parallel-stranded (ps) oligonucleotide duplexes containing several new base pairs formed between 7-deazaisoguanine and cytosine, 8-aza-7-deaza-isoguanine and cytosine, and 5-aza-7-deaza guanine and guanine are described. The stability of the ps-hybrids increased if the duplex contains 8-aza-7-deazaisoguanine instead of isoguanine and is decreased by 7-deazaisoguanine incorporation. The purine-purine base pair between 5-aza-7-deazaguanine and guanine was found to be more stable than that of 5-methylisocytosine with guanine.

  DOI：

  10.1080/07328319908044781
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 sodium methylate 、 sodium hydride 、 苯硫酚 作用下， 以 甲醇 、 乙二醇 、 乙腈 为溶剂， 反应 2.0h， 生成 4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one
  参考文献：
  名称：

  Artificial Genetic Systems:  Exploiting the “Aromaticity” Formalism To Improve the Tautomeric Ratio for Isoguanosine Derivatives

  摘要：

  The tautomerism of 2'-deoxy-7-deaza-isoguanosine (2) was studied and compared to that of 2'-deoxyisoguanosine (1). The fixed N-1-methyl (8) and O-methyl (4) derivatives were synthesized to represent the pure extremes of each tautomer. The replacement of the imidazole ring in 1 with a pyrrole ring in 2 makes the keto form in the latter more favored by 2 orders of magnitude (K-TAUT for 2 approximate to 10(3), as opposed to K-TAUT for 1 approximate to 10).

  DOI：

  10.1021/jo0497959

文献信息

• Base-Pairing, Tautomerism, and Mismatch Discrimination of 7-Halogenated 7-Deaza-2‘-deoxyisoguanosine:  Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation
  作者：Frank Seela、Xiaohua Peng、Hong Li

  DOI：10.1021/ja0425785

  日期：2005.6.1

  Oligonucleotides containing 2'-deoxyisoguanosine (1, iG(d)), 7-deaza-2'-deoxyisoguanosine (2, c(7)iG(d)), and its 7-halogenated derivatives 3 and 4 were synthesized on solid phase using the phosphoramidite building blocks 5-7. The hybridization properties of oligonucleotides were studied on duplexes with parallel and antiparallel chain orientation. It was found that the 7-halogenated nucleoside analogues

  在固相上合成含有 2'-脱氧异鸟苷 (1, iG(d))、7-deaza-2'-deoxyisoguanosine (2, c(7)iG(d)) 及其 7-卤代衍生物 3 和 4 的寡核苷酸使用亚磷酰胺积木 5-7。在具有平行和反平行链方向的双链体上研究了寡核苷酸的杂交特性。发现 7-卤代核苷类似物 3 和 4 显着增强了平行 (ps) 和反平行 (aps) DNA 中的双链体稳定性。此外，卤化核苷将互变异构酮-烯醇平衡强烈地转向酮形式，K(TAUT) [酮]/[烯醇] 大约 10(4) 接近 2'-脱氧鸟苷 (10(4)- 10(5))，而非卤化的 7-deaza-2' -脱氧异鸟苷 2 的 K(TAUT) 约为 2000，1 的烯醇浓度在水溶液中为 10%。因此，在反平行和平行 DNA 中，核苷 3 和 4 对 dT 的错配辨别能力比化合物 1 或 2 好得多。与 1 或 2 相比，预期
• 2?-Deoxyisoguanosine and Base-Modified Analogues: Chemical and Photochemical Synthesis
  作者：Zygmunt Kazimierczuk、Ralf Mertens、Wieslaw Kawczynski、Frank Seela

  DOI：10.1002/hlca.19910740816

  日期：1991.12.11

  synthesis of 2′-deoxyisoguanosine (2), and the pyrrolo[2,3-d]pyrimidine and pyrazolo[3,4-d]pyrimidine 2′-deoxyribonucleosides 3 and 4 is described. Condensation of the imidazole precursor 5 with benzoyl isocyanate followed by reaction with ammonia gave 2. Its N(7) regioisomer was obtained from 6. Compound 2 was also prepared by the photochemically induced conversion of 2-Chloro- and 2-bromopurine 2′-deoxyribofuranosides

  描述了2'-脱氧异鸟苷（2），吡咯并[2,3- d ]嘧啶和吡唑并[3,4- d ]嘧啶2'-脱氧核糖核苷3和4的合成。咪唑前体5与苯甲酰基异氰酸酯缩合，然后与氨反应，得到2。它的N（7）区域异构体是从6获得的。还通过分别在水溶液中将2-氯-和2-溴嘌呤2'-脱氧核糖呋喃糖苷9a和10进行光化学诱导的转化来制备化合物2，进一步将光反应用于化合物3的合成。和4分别从氨基-氯-2'-脱氧核苷9b和9c开始。
• Furanoside–pyranoside isomerization of tubercidin and its 2′-deoxy derivatives: influence of nucleobase and sugar structure on the proton-catalysed reaction
  作者：Frank Seela、Sabine Menkhoff、Silvia Behrendt

  DOI：10.1039/p29860000525

  日期：——

  2′-Deoxy-2-methoxytubercidin (6a) which was prepared from the nucleobase (1a) with the halogenose (2)via phase-transfer glycosylation isomerizes rapidly under acidic conditions. Two pyranosides [(7a) and (8a)] and the anomeric furanoside (5a) are formed. The isomerization process was followed kinetically, demonstrating that furanoside formation is kinetically controlled whereas the β-pyranoside (7a)

  由核苷碱基（1a）与卤代糖（2）经由相转移糖基化反应制得的2'-脱氧-2-甲氧基微球蛋白（6a）在酸性条件下迅速异构化。形成两个吡喃糖苷[（（7a）和（8a）]]和异头呋喃糖苷（5a）。动力学上遵循异构化过程，表明呋喃糖苷的形成在动力学上受到控制，而β-吡喃糖苷（7a）是热力学上最稳定的产物。与（6a）相比，从2'-脱氧结核菌素（6b）获得了相似的结果，但异构化较慢。核糖核苷结核菌素（6c）仅在强酸处理下才异构化，通过裂解N-糖基键产生α-呋喃糖苷（5c）和核碱基（1c）。
• 7-Deazaisoguanine quartets: self-assembled oligonucleotides lacking the Hoogsteen motif
  作者：Frank Seela

  DOI：10.1039/a704866a

  日期：——

  Oligonucleotides containing consecutive 7-deazaisoguanine residues form self-assembled quartets, indicating that the purine nitrogen-7 of isoguanine is not participating in the hydrogen bonding pattern.

  含有连续 7-去氮异鸟嘌呤残基的寡核苷酸形成了自组装四元组，表明异鸟嘌呤的嘌呤氮-7 没有参与氢键模式。
• Molecular recognition systems with pyrimidine analog pairing
  申请人：Hoshika Shuichi

  公开号：US10370706B1

  公开（公告）日：2019-08-06

  This invention covers a new molecular recognition system, where duplexes of DNA-like molecules comprise segments built from nucleotides that carry only a small pyrimidine-like analog, and where the segments pair by pyrimidine analog:pyrimidine analog “skinny” pairing. This pairing retains hydrogen bonding complementarity. Further, this invention relates to processes for preparing those duplexes, and processes that use such duplexes as primer:template complexes for reactions catalyzed by DNA polymerases.

  本发明涉及一种新的分子识别系统，在这种系统中，DNA 样分子的双链包括由核苷酸构建的片段，这些核苷酸只携带一种小的嘧啶类似物，这些片段通过嘧啶类似物：嘧啶类似物的 "瘦 "配对配对。这种配对保留了氢键互补性。此外，本发明还涉及制备这些双链体的工艺，以及将这些双链体用作 DNA 聚合酶催化反应的引物：模板复合物的工艺。