N²-isobutyryl-2',3'-O-dibenzoyl-5'-O-(4,4'-dimethoxytrityl)guanosine | 105038-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N²-isobutyryl-2',3'-O-dibenzoyl-5'-O-(4,4'-dimethoxytrityl)guanosine
• 英文别名: [(2R,3R,4R,5R)-4-benzoyloxy-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-[2-(2-methylpropanoylamino)-6-oxo-3H-purin-9-yl]oxolan-3-yl] benzoate
• CAS: 105038-57-1
• 化学式: C₄₉H₄₅N₅O₁₀
• 分子量: 863.924
• InChiKey: XFTQLGJSEFTMNJ-BHSJWVCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  64.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  182.19
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N²-isobutyryl-2',3'-O-dibenzoyl-5'-O-(4,4'-dimethoxytrityl)guanosine 在 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4R,5R)-2-(6-((3,4-dimethoxybenzyl)oxy)-2-isobutyramido-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  3,4-二甲氧基苄基基团在寡核苷酸合成中作为2'-羟基基团的保护基团的用途

  摘要：

  通过核苷与 3,4-二甲氧基苄基三氯乙酰亚胺或 3,4-二甲氧基苄基溴-NaH 的反应，将 3,4-二甲氧基苄基引入 2'-羟基。此外，该基团可用作鸟嘌呤残基的O6-酰胺基团的保护基团。受保护的核苷是合成寡核糖核苷酸的有用起始材料。通过用氧化剂处理，3,4-二甲氧基苄基从寡核糖核苷酸中迅速去除，而对糖苷键没有任何损害。

  DOI：

  10.1246/cl.1986.1005
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.5h， 生成 N²-isobutyryl-2',3'-O-dibenzoyl-5'-O-(4,4'-dimethoxytrityl)guanosine
  参考文献：
  名称：

  Synthesis, characterization, and biological properties of small branched RNA fragments containing chiral (R_pand S_p) 2′,5′-phosphorothioate linkages

  摘要：

  Synthetic branched RNA fragments were prepared to examine the stereochemical requirements for hydrolysis of RNA lariats by the yeast debranching enzyme (yDBR). Specifically, two branched trinucleoside diphosphates and a tetranucleoside triphosphate containing a 2',5'-linked phosphorothioate linkage of defined stereochemistry, namely R-p-A(2'ps5'G)pC, S-p-A(2'ps5'G)pC and S-p-ApA(2'ps5'G)pC, were prepared via solution-phase methods. Unlike the all-phosphodiester control, A(2'p5'G)pC, the R-p-thioated trimer was not cleaved by yDBR, demonstrating that changing the pro-R-p oxygen at the 2',5'-phosphodiester bond averts hydrolysis by the enzyme. In contrast, the S-p branched compounds (trimer and tetramer) were cleaved yDBR, albeit with reduced efficiency relative to the corresponding all-phosphodiester branched compounds. Furthermore, the small branched RNAs (5 nt) were not cleaved as efficiently as a 18-nt bRNA, suggesting that the enzyme appears to have a stronger preference for larger bRNA substrates. The non-hydrolyzable branched RNA fragments prepared during these studies may be promising candidates for the future co-crystallization and X-ray analyses of DBR:bRNA complexes.

  DOI：

  10.1080/15257770500447004

文献信息

• Fujii, Masayo; Horinouchi, Yuzoh; Takaku, Hiroshi, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 7, p. 3066 - 3069
  作者：Fujii, Masayo、Horinouchi, Yuzoh、Takaku, Hiroshi

  DOI：——

  日期：——
• ROZNERS, EH. Z.;REKIS, A. X.;KUMPINSH, V. X.;BIZDENA, EH. O., BIOORGAN. XIMIYA, 16,(1990) N1, S. 1531-1536
  作者：ROZNERS, EH. Z.、REKIS, A. X.、KUMPINSH, V. X.、BIZDENA, EH. O.

  DOI：——

  日期：——
• FUJII, MASAYO;HORINOUCHI, YUZOH;TAKAKU, HIROSHI, CHEM. AND PHARM. BULL., 35,(1987) N 7, 3066-3069
  作者：FUJII, MASAYO、HORINOUCHI, YUZOH、TAKAKU, HIROSHI

  DOI：——

  日期：——