2,3-dihydro-2-hydroxymethylfuran-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,3-dihydro-2-hydroxymethylfuran-3-one
• 英文别名: (2R)-2-(hydroxymethyl)furan-3-one
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: MCPPEQAMTFKQFR-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-N-benzoyl-9-(3,5-O-isopropylidene-3-C-vinyl-β-D-xylofuranosyl)adenine 在 吡啶 、 potassium permanganate 、 phosphate buffer 、 水 、 三正丁基氢锡 、 臭氧 、 二氯磷酸苯酯 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 7.5h， 生成 2,3-dihydro-2-hydroxymethylfuran-3-one
  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

文献信息

• Studies on the Mechanism of Ribonucleotide Reductases
  作者：Roman Lenz、Bernd Giese

  DOI：10.1021/ja962974q

  日期：1997.3.1

  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.