3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine | 1173243-10-1

• 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: 3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
• CAS: 1173243-10-1
• 化学式: C₄₀H₄₇N₉O₅
• 分子量: 733.87
• InChiKey: DPFRNDJLKIYEKP-ZXZAZSCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.35
• 重原子数：
  54.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  165.11
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine 在 三苯基膦 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 6-N-[(di-n-butylamino)methylene]-3'-{[N-allyloxycarbonyl-S-(tert-butylthio)-L-cysteinyl]amino}-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
  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：

  (2R,3S,4R,5S)-4-azido-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-2-(6-(((dibutylamino)methylene)amino)-9H-purin-9-yl)tetrahydrofuran-3-yl trifluoromethanesulfonate 在 18-冠醚-6 、 potassium trifluoroacetate 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以578 mg的产率得到3'-azido-6-N-[(di-n-butylamino)methylene]-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-β-D-adenosine
  参考文献：
  名称：

  Moroder, Holger; Steger, Jessica; Graber, Dagmar, Angewandte Chemie - International Edition, 2009, vol. 48, p. 4056 - 4060

  摘要：

  DOI：

文献信息

• The Synthesis of Methylated, Phosphorylated, and Phosphonated 3′-Aminoacyl-tRNA^SecMimics
  作者：Lukas Rigger、Rachel L. Schmidt、Kaitlyn M. Holman、Miljan Simonović、Ronald Micura

  DOI：10.1002/chem.201302188

  日期：2013.11.18

  accurate synthesis of methylated, phosphorylated, and phosphonated serinyl‐derived tRNASec mimics that contain a hydrolysis‐resistant ribose 3′‐amide linkage instead of the natural ester bond. The procedures introduced allow for efficient site‐specific methylation and/or phosphorylation directly on the solid support utilized in the automated RNA synthesis. For the preparation of (S)‐2‐amino‐4‐phosphonobutyric

  第二十一个氨基酸，硒代半胱氨酸 (Sec)，是生命所有领域中唯一在其同源转移 RNA (tRNA Sec ) 上合成的氨基酸。多步骤途径涉及O-磷酸丝氨酰-tRNA：硒代半胱氨酰-tRNA 合酶 (SepSecS)，这是一种催化末端化学反应的酶，在此过程中，磷酸丝氨酰-tRNA Sec中间体转化为硒代半胱氨酰-tRNA Sec。SepSecS 架构和 tRNA Sec模式最近在原子分辨率下确定了识别。晶体结构提供了有价值的见解，这些见解引起了由于缺乏适当的分子探针而无法验证的机制建议。为了进一步提高我们对一般硒代半胱氨酸生物合成机制和特别是 SepSecS 机制的理解，需要稳定的 tRNA Sec底物，该底物带有模拟特定反应中间体的氨酰基部分。在这里，我们报告了甲基化、磷酸化和磷酸化丝氨酰衍生 tRNA Sec的准确合成含有耐水解核糖 3'-酰胺键而不是天然酯键的模拟物。引入的程序允许直接在自动化
• Efficient Access to Nonhydrolyzable Initiator tRNA Based on the Synthesis of 3′-Azido-3′-Deoxyadenosine RNA
  作者：Jessica Steger、Dagmar Graber、Holger Moroder、Anna-Skrollan Geiermann、Michaela Aigner、Ronald Micura

  DOI：10.1002/anie.201003424

  日期：——

  3′‐aminoacyl‐tRNA conjugates that contain a stable amide linkage instead of the natural ester are valuable substrates for biochemical studies of ribosomal processes. In a novel preparation of the stable E. coli initiator tRNA derivative 3′‐(N‐formylmethionyl)amino‐tRNAfMet the key feature is the synthesis of 3′‐azido oligoribonucleotides using a new functionalized solid support.

  灵活运用：含有稳定酰胺键而非天然酯的耐水解 3'-氨基酰基-tRNA 偶联物是核糖体过程生化研究的宝贵底物。在稳定的大肠杆菌起始 tRNA 衍生物 3'-( N-甲酰基甲硫氨酰基)氨基-tRNA fMet的新制备中，关键特征是使用新的功能化固体支持合成 3'-叠氮基寡核糖核苷酸。
• Functionalized polystyrene supports for solid-phase synthesis of glycyl-, alanyl-, and isoleucyl-RNA conjugates as hydrolysis-resistant mimics of peptidyl-tRNAs
  作者：Jessica Steger、Ronald Micura

  DOI：10.1016/j.bmc.2011.07.018

  日期：2011.9

  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.