7-(3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine | 902452-70-4

• 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: 7-(3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine
• CAS: 902452-70-4
• 化学式: C₂₂H₂₅N₅O₆
• 分子量: 455.47
• InChiKey: KZCJEBAPCMCWFL-HRSBRNJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  140.59
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-(3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine 在 palladium on activated charcoal 甲酸 作用下， 以 甲醇 为溶剂， 以81%的产率得到N-[7-((1S,3R,4R,7S)-7-Hydroxy-1-hydroxymethyl-2,5-dioxa-bicyclo[2.2.1]hept-3-yl)-6-oxo-6,7-dihydro-1H-purin-2-yl]-isobutyramide
  参考文献：
  名称：

  Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine

  摘要：

  The method for scaled-up production of alpha-L-LNA phosphoramidite building blocks containing thymine and 5-methylcytosine nucleobases is described. Binding properties of pyrimidine TFOs modified with alpha-L-LNA are reported. In contrast to LNA TFOs, the fully modified a-L-LNA forms a stable triplex with a model DNA duplex. Pyrimidine DNA/LNA/alpha-L-LNA chimeras also efficiently hybridize with a model DNA duplex in the parallel mode. LNA nucleoside containing unnatural N-7-glycosylated guanine (LNA-(7) G) was synthesized by a convergent method and incorporated into LNA oligonucleotides. The triplex-forming alternating DNA/LNA oligonucleotides containing a single LNA-(7) G modification instead of internal LNA-mC demonstrate improved pH-dependent properties. The single LNA-(7) G modification can also discriminatively reduce competitive binding of TFOs to natural nucleic acids in the antiparallel duplex mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.016
• 作为产物：
  描述：

  7-(2-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxy-5-O-methanesulfonyl-β-D-erythro-pentofuranosyl)-2-N-isobutyrylguanine 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-(3-O-benzyl-2-O,4-C-methylene-β-D-ribofuranosyl)-2-N-isobutyrylguanine
  参考文献：
  名称：

  Conformationally restricted triplex-forming oligonucleotides (TFOs). Binding properties of α-l-LNA and introduction of the N7-glycosylated LNA-guanosine

  摘要：

  The method for scaled-up production of alpha-L-LNA phosphoramidite building blocks containing thymine and 5-methylcytosine nucleobases is described. Binding properties of pyrimidine TFOs modified with alpha-L-LNA are reported. In contrast to LNA TFOs, the fully modified a-L-LNA forms a stable triplex with a model DNA duplex. Pyrimidine DNA/LNA/alpha-L-LNA chimeras also efficiently hybridize with a model DNA duplex in the parallel mode. LNA nucleoside containing unnatural N-7-glycosylated guanine (LNA-(7) G) was synthesized by a convergent method and incorporated into LNA oligonucleotides. The triplex-forming alternating DNA/LNA oligonucleotides containing a single LNA-(7) G modification instead of internal LNA-mC demonstrate improved pH-dependent properties. The single LNA-(7) G modification can also discriminatively reduce competitive binding of TFOs to natural nucleic acids in the antiparallel duplex mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.04.016