3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine | 1345543-66-9

• 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: 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine
• CAS: 1345543-66-9
• 化学式: C₂₇H₄₅N₇O₅S₂Si
• 分子量: 639.916
• InChiKey: AEENAFKLXPAYTM-VNTMZGSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  155.51
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  四氢-2,6-二氧代-2H-吡喃-3-丙酸 、 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine 在 吡啶 作用下， 反应 6.0h， 以98%的产率得到3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-N6,N6-{2-[3-(2-carboxyethyl)]glutaryl}-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Native Chemical Ligation of Hydrolysis-Resistant 3′-Peptidyl–tRNA Mimics

  摘要：

  Hydrolysis-resistant 3'-peptidyl-RNA conjugates that mimic tRNA termini represent a remarkable synthetic challenge, particularly if they contain amino acids with complex side-chain functionalities, such as arginines. Here we demonstrate a novel approach that combines solid-phase synthesis and bioconjugation to obtain these derivatives with high efficiency and purity. The key step is native chemical ligation of 3'-cysteinyl-RNA fragments to highly soluble peptide thioesters. The so-prepared 3'-peptidyl-RNA conjugates relate to resistance peptides that can render the ribosome resistant to macrolide antibiotics by a yet unknown ribosomal translation mechanism.

  DOI：

  10.1021/ja209053b
• 作为产物：
  描述：

  S-叔丁基硫-L-半胱氨酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium carbonate 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 3'-N-[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]-5'-O-(tert-butyldimethylsilyl)-9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Native Chemical Ligation of Hydrolysis-Resistant 3′-Peptidyl–tRNA Mimics

  摘要：

  Hydrolysis-resistant 3'-peptidyl-RNA conjugates that mimic tRNA termini represent a remarkable synthetic challenge, particularly if they contain amino acids with complex side-chain functionalities, such as arginines. Here we demonstrate a novel approach that combines solid-phase synthesis and bioconjugation to obtain these derivatives with high efficiency and purity. The key step is native chemical ligation of 3'-cysteinyl-RNA fragments to highly soluble peptide thioesters. The so-prepared 3'-peptidyl-RNA conjugates relate to resistance peptides that can render the ribosome resistant to macrolide antibiotics by a yet unknown ribosomal translation mechanism.

  DOI：

  10.1021/ja209053b