N⁶-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside | 1541908-47-7

• 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: N⁶-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside
• CAS: 1541908-47-7
• 化学式: C₄₃H₄₁N₅O₉
• 分子量: 771.827
• InChiKey: GURPZKSFXCWBDT-MXTDFSNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  57.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  173.22
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N⁶-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以97%的产率得到N⁶-benzoyl-2′-O-(4,4′-dimethoxytrityl)-3′-O-[(2-cyanoethyl-N,N-diisopropyl)phosphoramidite]-5′-O-levulinyl-adenosine-9-β-D-arabinofuranoside
  参考文献：
  名称：

  Regiospecific Solid-Phase Synthesis of Branched Oligoribonucleotides That Mimic Intronic Lariat RNA Intermediates

  摘要：

  We have developed new solid phase methods for the synthesis of branched RNAs that mimic intronic lariat RNA intermediates. These methods produce branched oligoribonucleotide sequences of arbitrary length, base composition, and regiochemistry at the branchpoint junction. The methods utilize branching monomers that allow for the growth of each branch regioselectively from any of the hydroxyl positions (5', 3', or 2') at the branch-point junction. The integrity and branchpoint connectivity of the synthetic products have been confirmed by HPLC and MS analysis, and cleavage of the 2',5' linkage by recombinant debranching enzyme. Nonhydrolyzable branched RNA analogues containing arabinose instead of ribose at the branchpoint junction were shown to inhibit debranching activity and, hence, represent "decoys" for sequestering RNA binding proteins thought to drive amyotrophic lateral sclerosis (ALS).

  DOI：

  10.1021/jo4024182
• 作为产物：
  描述：

  N⁶-benzoyl-2′-O-levulinyl-3′,5′-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-adenosine-9-β-D-arabinofuranoside 在 吡啶 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 N⁶-benzoyl-2′-O-levulinyl-5′-O-[4,4′-dimethoxytrityl]-adenosine-9-β-D-arabinofuranoside
  参考文献：
  名称：

  Regiospecific Solid-Phase Synthesis of Branched Oligoribonucleotides That Mimic Intronic Lariat RNA Intermediates

  摘要：

  We have developed new solid phase methods for the synthesis of branched RNAs that mimic intronic lariat RNA intermediates. These methods produce branched oligoribonucleotide sequences of arbitrary length, base composition, and regiochemistry at the branchpoint junction. The methods utilize branching monomers that allow for the growth of each branch regioselectively from any of the hydroxyl positions (5', 3', or 2') at the branch-point junction. The integrity and branchpoint connectivity of the synthetic products have been confirmed by HPLC and MS analysis, and cleavage of the 2',5' linkage by recombinant debranching enzyme. Nonhydrolyzable branched RNA analogues containing arabinose instead of ribose at the branchpoint junction were shown to inhibit debranching activity and, hence, represent "decoys" for sequestering RNA binding proteins thought to drive amyotrophic lateral sclerosis (ALS).

  DOI：

  10.1021/jo4024182