7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate | 227950-65-4

• 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: 7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
• 英文别名: [7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(2-methylpropanoylamino)pyrrolo[2,3-d]pyrimidin-2-yl] N,N-diphenylcarbamate
• CAS: 227950-65-4
• 化学式: C₂₈H₂₉N₅O₆
• 分子量: 531.568
• InChiKey: PEUFXHWEERNRNW-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 在 N,N-二异丙基乙胺 作用下， 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'-(2-cyanoethyl diisopropylphosphoramidite)
  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
• 作为产物：
  描述：

  4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one 在 吡啶 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 生成 7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-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.
• The Base-Pairing Properties of 7-Deaza-2′-deoxyisoguanosine and 2′-Deoxyisoguanosine in Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation
  作者：Frank Seela、Changfu Wei

  DOI：10.1002/(sici)1522-2675(19990505)82:5<726::aid-hlca726>3.0.co;2-k

  日期：1999.5.5

  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.