2'-O-CEM-3'-O-TBDMS-N6-acetyladenosine | 1092506-75-6

• 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: 2'-O-CEM-3'-O-TBDMS-N6-acetyladenosine
• CAS: 1092506-75-6
• 化学式: C₂₂H₃₄N₆O₆Si
• 分子量: 506.634
• InChiKey: MSXZXCOIAYGHEV-QTQZEZTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  153.64
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-O-CEM-3'-O-TBDMS-N6-acetyladenosine 、 在 1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate 、 2,6-二甲基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Chemical synthesis of diastereomeric diadenosine boranophosphates (ApbA) from 2′-O-(2-cyanoethoxymethyl)adenosine by the boranophosphotriester method

  摘要：

  We have synthesized diastereomerically pure diadenosine 3 ',5 '-boranophosphates (Ap(b)A) by using the boranophosphotriester method from ribonucleosides protected with the 2 '-hydroxy protecting group 2-cyanoethoxymethyl (CEM). Melting curves of the triple-helical complex of the dimer ApbA and 2poly(U) at high ionic strength revealed that presumptive (Sp)-Ap(b)A had a much higher affinity and presumptive (Rp)-Ap(b)A a much lower affinity for poly(U) than the natural dimer ApA did. In contrast, the affinities of these dimers for poly(dT) were similar. Both the (Rp)- and the (Sp)-boranophosphate diastereomers showed much higher resistance to digestion by snake venom phosphodiesterase and nuclease P1 than ApA did. They have potential for use as synthons to be incorporated into boranophosphate oligonucleotides. In particular, because oligonucleotides containing Sp boranophosphate nucleotides are expected to bind more strongly and specifically to RNA than natural oligoribonucleotides do, they may find application in the isolation and detection of functional RNA in basic research and diagnostics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.040
• 作为产物：
  描述：

  在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以68%的产率得到2'-O-CEM-3'-O-TBDMS-N6-acetyladenosine
  参考文献：
  名称：

  Chemical synthesis of diastereomeric diadenosine boranophosphates (ApbA) from 2′-O-(2-cyanoethoxymethyl)adenosine by the boranophosphotriester method

  摘要：

  We have synthesized diastereomerically pure diadenosine 3 ',5 '-boranophosphates (Ap(b)A) by using the boranophosphotriester method from ribonucleosides protected with the 2 '-hydroxy protecting group 2-cyanoethoxymethyl (CEM). Melting curves of the triple-helical complex of the dimer ApbA and 2poly(U) at high ionic strength revealed that presumptive (Sp)-Ap(b)A had a much higher affinity and presumptive (Rp)-Ap(b)A a much lower affinity for poly(U) than the natural dimer ApA did. In contrast, the affinities of these dimers for poly(dT) were similar. Both the (Rp)- and the (Sp)-boranophosphate diastereomers showed much higher resistance to digestion by snake venom phosphodiesterase and nuclease P1 than ApA did. They have potential for use as synthons to be incorporated into boranophosphate oligonucleotides. In particular, because oligonucleotides containing Sp boranophosphate nucleotides are expected to bind more strongly and specifically to RNA than natural oligoribonucleotides do, they may find application in the isolation and detection of functional RNA in basic research and diagnostics. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.040