2',3'-bis(tert-butyldimethylsilyl)guanosine-5'-O-(β-cyanoethyl-N,N-diisopropylphosphoramidite) | 860030-75-7

• 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',3'-bis(tert-butyldimethylsilyl)guanosine-5'-O-(β-cyanoethyl-N,N-diisopropylphosphoramidite)
• 英文别名: 5'-O-(2-cyanoethyl-N,N'-diisopropylaminophosphino)-2',3'-di-O-(tert-butyldimethylsilyl)guanosine
• CAS: 860030-75-7
• 化学式: C₃₁H₅₈N₇O₆PSi₂
• 分子量: 711.99
• InChiKey: JKQCLQJMTGLFCX-OPFFINDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  47.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  162.77
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2',3'-bis(tert-butyldimethylsilyl)guanosine-5'-O-(β-cyanoethyl-N,N-diisopropylphosphoramidite) 在 咪唑 三氟甲磺酸盐 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Efficient Preparation of Organic Substrate−RNA Conjugates via in Vitro Transcription

  摘要：

  A concise synthetic way has been developed for the preparation of guanosine monophosphate derivatives carrying a decaethylene glycol spacer at their 5'-oxygen to which are attached a range of organic substrates. The four different compounds, prepared via a convergent synthetic strategy, carry a tethered benzylallyl ether residue (1a), an anthracene (1b), a benzyl carbamate residue (1c), or a primary amino group (1d), respectively. All four compounds have been successfully incorporated at the T-end of a 25-mer long RNA transcript via T7 RNA polymerase, and no inhibition of chain elongation could be observed. Under proper conditions, 1a and 1b can be incorporated up to 90-95% and 1c up to 68%. The amino-terminated initiator Id is incorporated less efficiently although still up to 49%. These results show that the more hydrophobic the guanosine monophosphate derivative is, the higher is its enzymatic incorporation.

  DOI：

  10.1021/ja051179m
• 作为产物：
  描述：

  2',3'-O-bis(tert-butyldimethylsilyl)-guanosine 、 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 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到2',3'-bis(tert-butyldimethylsilyl)guanosine-5'-O-(β-cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Efficient Preparation of Organic Substrate−RNA Conjugates via in Vitro Transcription

  摘要：

  A concise synthetic way has been developed for the preparation of guanosine monophosphate derivatives carrying a decaethylene glycol spacer at their 5'-oxygen to which are attached a range of organic substrates. The four different compounds, prepared via a convergent synthetic strategy, carry a tethered benzylallyl ether residue (1a), an anthracene (1b), a benzyl carbamate residue (1c), or a primary amino group (1d), respectively. All four compounds have been successfully incorporated at the T-end of a 25-mer long RNA transcript via T7 RNA polymerase, and no inhibition of chain elongation could be observed. Under proper conditions, 1a and 1b can be incorporated up to 90-95% and 1c up to 68%. The amino-terminated initiator Id is incorporated less efficiently although still up to 49%. These results show that the more hydrophobic the guanosine monophosphate derivative is, the higher is its enzymatic incorporation.

  DOI：

  10.1021/ja051179m

文献信息

• RNA–peptide conjugate synthesis by inverse-electron demand Diels–Alder reaction
  作者：Sandeep Ameta、Juliane Becker、Andres Jäschke

  DOI：10.1039/c4ob00076e

  日期：——

  We present an efficient method to synthesize RNA–peptide conjugates employing inverse Diels–Alder cycloaddition. Different dienophiles are enzymatically incorporated into RNA and then conjugated with a tetrazine peptide at 1 : 1 stoichiometry.

  我们提出了一种高效的方法，利用反Diels-Alder环加成合成RNA-肽共轭物。不同的二烯丙烷酮通过酶催化被合成到RNA中，然后以1：1的化学计量比与四氮杂环肽结合。