6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine | 188486-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine
• 英文别名: (4aR,6R,7R,7aS)-7-acetyloxy-6-(6-benzamidopurin-9-yl)-2,2-dimethyl-4,4a,6,7-tetrahydrofuro[3,2-d][1,3]dioxine-7a-carboxylic acid
• CAS: 188486-39-7
• 化学式: C₂₃H₂₃N₅O₈
• 分子量: 497.464
• InChiKey: ORUXKZAJCVXWOO-DZPMHROLSA-N

物化性质

• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  163.99
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-β-D-xylofuranosyl)adenine 在 氘代甲醇 、 水 、 氘代三正丁基锡 、 二氯磷酸苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成
  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-O-acetyl-3,5-O-isopropylidene-3-C-vinyl-β-D-xylofuranosyl)adenine 在 potassium permanganate 、 phosphate buffer 、 臭氧 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 生成 6-N-benzoyl-9-(2-O-acetyl-3-C-carboxy-3,5-O-isopropylidene-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