6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-carboxy-β-D-xylofuranosyl)adenine | 188486-31-9

• 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: 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-carboxy-β-D-xylofuranosyl)adenine
• 英文别名: (2R,3S,4R,5R)-5-(6-benzamidopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxyoxolane-3-carboxylic acid
• CAS: 188486-31-9
• 化学式: C₃₀H₄₅N₅O₇Si₂
• 分子量: 643.888
• InChiKey: DAFKOBLGJWQGRU-OQUQFALVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  157.92
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-carboxy-β-D-xylofuranosyl)adenine 在 N,N'-羰基二(1,2,4-三氮唑) 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-N-benzoyl-9-(2-O-(tert-butyldimethylsilyl)-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Studies on the Mechanism of Ribonucleotide Reductases

  摘要：

  Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 . 10(6) s(-1) in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 10(3) times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

  DOI：

  10.1021/ja962974q
• 作为产物：
  描述：

  6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-O-(trimethylsilyl)-3-C-vinyl-β-D-xylofuranosyl)adenine 在 盐酸 、 potassium permanganate 、 phosphate buffer 、 水 、 臭氧 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 5.0h， 生成 6-N-benzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-3-C-carboxy-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Studies on the Mechanism of Ribonucleotide Reductases

  摘要：

  Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 . 10(6) s(-1) in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 10(3) times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

  DOI：

  10.1021/ja962974q