6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine | 1333992-33-8

• 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: 6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
• CAS: 1333992-33-8
• 化学式: C₆₁H₇₀N₈O₈
• 分子量: 1043.28
• InChiKey: NNPQOXILUUPEKF-UZIOHEBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.11
• 重原子数：
  77.0
• 可旋转键数：
  24.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  183.78
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine 、 adipic acid bis(pentafluorophenyl)ester 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 2.0h， 以79%的产率得到6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-O-[1,6-dioxo-6-(pentafluorophenyloxy)hexyl]-β-D-adenosine
  参考文献：
  名称：

  Functionalized polystyrene supports for solid-phase synthesis of glycyl-, alanyl-, and isoleucyl-RNA conjugates as hydrolysis-resistant mimics of peptidyl-tRNAs

  摘要：

  RNA-peptide conjugates that mimic amino acid-charged tRNAs and peptidyl-tRNAs are of high importance for structural and functional investigations of ribosomal complexes. Here, we present the synthesis of glycyl-, alanyl-, and isoleucyladenosine modified solid supports that are eligible for the synthesis of stable 3'-aminoacyl- and 3'-peptidyl-tRNA termini with an amide instead of the natural ester linkage. The present work significantly expands the range of accessible peptidyl-tRNA mimics for ribosomal studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.018
• 作为产物：
  描述：

  3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine 、 Fmoc-L-Ile-OBt 在 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 以304 mg的产率得到6-N-[(di-n-butylamino)methylene]-3'-{[N-(9-fluorenyl)methoxycarbonyl-L-isoleucyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
  参考文献：
  名称：

  Functionalized polystyrene supports for solid-phase synthesis of glycyl-, alanyl-, and isoleucyl-RNA conjugates as hydrolysis-resistant mimics of peptidyl-tRNAs

  摘要：

  RNA-peptide conjugates that mimic amino acid-charged tRNAs and peptidyl-tRNAs are of high importance for structural and functional investigations of ribosomal complexes. Here, we present the synthesis of glycyl-, alanyl-, and isoleucyladenosine modified solid supports that are eligible for the synthesis of stable 3'-aminoacyl- and 3'-peptidyl-tRNA termini with an amide instead of the natural ester linkage. The present work significantly expands the range of accessible peptidyl-tRNA mimics for ribosomal studies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.018