6-N-benzoyl-2',3'-O-bis-tetrahydropyranyl-β-D-arabinoadenosine | 1357015-83-8

• 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: 6-N-benzoyl-2',3'-O-bis-tetrahydropyranyl-β-D-arabinoadenosine
• CAS: 1357015-83-8
• 化学式: C₂₇H₃₃N₅O₇
• 分子量: 539.588
• InChiKey: INZHYWRVZWLBKM-QKHNVQEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  139.08
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-2',3'-O-bis-tetrahydropyranyl-β-D-arabinoadenosine 在 吡啶 、 2,6-二甲基吡啶 、 三甲基溴硅烷 、 silver trifluoromethanesulfonate 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 80.0h， 生成
  参考文献：
  名称：

  Activation of human RNase L by 2′- and 5′-O-methylphosphonate-modified oligoadenylates

  摘要：

  To determine the influence of internucleotide linkage and sugar ring conformation, and the role of 5'-terminal phosphate, on the activation of human RNase L, a series of 2'- and 5'-O-methylphosphonate-modified tetramers were synthesized from appropriate monomeric units and evaluated for their ability to activate human RNase L. Tetramers pAAApcX modified by ribo, arabino or xylo 5'-phosphonate unit p(c)X activated RNase L with efficiency comparable to that of natural activator. Moreover, incorporation of phosphonate linkages ensured the stability against cleavage by nucleases. The substitution of 5'-terminal phosphate for 5'-terminal phosphonate in tetramer p(c)XAAA afforded tetramers with excellent activation efficiency and with complete stability against cleavage by phosphomonoesterases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.040