4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate | 198008-12-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
• 英文别名: [4-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidin-2-yl] N,N-diphenylcarbamate
• CAS: 198008-12-7
• 化学式: C₂₄H₂₃N₅O₅
• 分子量: 461.477
• InChiKey: JZEUEQDTMYXHCJ-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 在 N-甲基吗啉 、 吡啶 、 1H-1,2,4-三唑 、 三甲基氯硅烷 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.08h， 生成 7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 3'-triethylammonium phosphonate
  参考文献：
  名称：

  The Base-Pairing Properties of 7-Deaza-2′-deoxyisoguanosine and 2′-Deoxyisoguanosine in Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation

  摘要：

  Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'-deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu = ib) residue fur the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7-deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine.5-methylisocytosine was the most stable one in aps-DNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5-methylisocytosine, thymine, and guanine was observed in the case of aps-duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base-pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<726::aid-hlca726>3.0.co;2-k
• 作为产物：
  描述：

  (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 在 吡啶 、 ammonium hydroxide 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 1,4-二氧六环 为溶剂， 反应 72.0h， 生成 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
  参考文献：
  名称：

  7-Deazaisoguanine quartets: self-assembled oligonucleotides lacking the Hoogsteen motif

  摘要：

  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。

  DOI：

  10.1039/a704866a

文献信息

• Oligonucleotides Containing Consecutive 2′-Deoxy-Isoguanosine Residues: Synthesis, Parallel Duplex Formation and Identification of a d(T₄iG₄T₄) Tetraplex
  作者：Frank Seela、Changfu Wei、Alexander Melenewski

  DOI：10.1080/07328319708006221

  日期：1997.7

  Oligonucleotides containing consecutive 2'-deoxyisoguanosines were synthesized by using building blocks protected with a diphenylcarb-amoyl residue. Parallel duplexes were formed by iG(d)-dC base pairs and a tetraplex of d(T(4)iG(4)T(4)) was identified by ion exchange HPLC.
• Parallel-Stranded DNA Formed by New Base Pairs Related to the Isoguanine-Cytosine or Isocytosine-Guanine Motifs
  作者：Frank Seela、Changfu Wei、Alexander Melenewski、Yang He、Rita Kröschel、Elisabeth Feiling

  DOI：10.1080/07328319908044781

  日期：1999.6

  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.