5’-amino-5’-deoxy-2’,3’-bis(O-triethylsilyl)adenosine | 473907-69-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5’-amino-5’-deoxy-2’,3’-bis(O-triethylsilyl)adenosine
• 英文别名: 5'-amino-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine；9-[(2R,3R,4R,5R)-5-(aminomethyl)-3,4-bis(triethylsilyloxy)oxolan-2-yl]purin-6-amine
• CAS: 473907-69-6
• 化学式: C₂₂H₄₂N₆O₃Si₂
• 分子量: 494.785
• InChiKey: JQIXQRQQRXRZGN-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5’-amino-5’-deoxy-2’,3’-bis(O-triethylsilyl)adenosine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 5'-(2''-carboxymethylaziridino)-5'-deoxy-2',3'-bis(O-triethylsilyl)adenosine
  参考文献：
  名称：

  Expeditious synthesis of aziridine-based cofactor mimics

  摘要：

  S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00590-2
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 咪唑 、 二苯基膦叠氮化物 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.83h， 生成 5’-amino-5’-deoxy-2’,3’-bis(O-triethylsilyl)adenosine
  参考文献：
  名称：

  Expeditious synthesis of aziridine-based cofactor mimics

  摘要：

  S-Adenosyl-L-methionine mimics were synthesized in a linear fashion highlighting methodology that bypasses the need for adenine base protection. These aziridine-based cofactor mimics are envisioned as useful biochemical tools and potential therapeutic agents whose mechanism of action hinges upon aberrant methyltransferase enzymes. Aziridination of the 5' position of adenosine was effected by convergence of suitably protected 5'-aminoadenosine with various dibromopropionates. The economy and high yields for this route to said aziridine-based cofactors is highly amenable to large-scale chemistry which no doubt will be vital to their development as therapeutics and biochemical tools. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00590-2

文献信息

• Fluorescent DNA Labeling by N-Mustard Analogues of<i>S</i>-Adenosyl-<scp>L</scp>-Methionine
  作者：Yuhao Du、Charles E. Hendrick、Krysta S. Frye、Lindsay R. Comstock

  DOI：10.1002/cbic.201200438

  日期：2012.10.15

  Fluorescent DNA: Novel analogues of S‐adenosyl‐L‐methionine containing an azide and alkyne were synthesized and demonstrated to undergo efficient methyltransferase‐dependent DNA alkylation. These sequence‐specific DNA modifications were visualized after fluorescent labeling with click chemistry.

  荧光DNA：合成了包含叠氮化物和炔烃的S-腺苷-L-蛋氨酸的新类似物，并证明它们可以进行有效的甲基转移酶依赖性DNA烷基化反应。使用点击化学方法进行荧光标记后，可以看到这些序列特异的DNA修饰。
• <i>o</i>-Nitrobenzenesulfonamides in Nucleoside Synthesis:  Efficient 5‘-Aziridination of Adenosine
  作者：Scott G. Petersen、Scott R. Rajski

  DOI：10.1021/jo050205w

  日期：2005.7.1

  5'-Aziridinoadenylates of the form 1 and a related nitrogen mustard variant have been constructed using a novel variation of the Mitsunobu reaction. Such molecules allow conversion of biological methyltransferases into nucleoside transferases, thus providing powerful tools for investigating S-adenosyl-L-methionine (SAM)-dependent methylation. We present here a highly effective synthesis of such molecules that is amenable to aziridine diversification as well as elaboration of the base moiety so as to afford "bumped" cofactor mimics compatible with "hole"-bearing mutant proteins.
• Aziridination of γ,δ-dibromoethyl-2-pentenoate with primary amines: extension of the Gabriel–Cromwell reaction
  作者：Rachel L. Weller、Scott R. Rajski

  DOI：10.1016/j.tetlet.2004.06.005

  日期：2004.7

  Ethyl (E)-4,5-dibromo-2-pentenoate readily reacts with an assortment of primary amines in the presence of DBU to afford the corresponding conjugated aziridines in good to moderate yields. That the reaction is compatible with a nucleoside-derived amine suggests a broad scope of application. (C) 2004 Elsevier Ltd. All rights reserved.