3'-deuterioadenosine | 90124-46-2

• 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: 3'-deuterioadenosine
• 英文别名: adenosine-3'-d
• CAS: 90124-46-2
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 268.236
• InChiKey: OIRDTQYFTABQOQ-ZWCBNAMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  139.54
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3'-deuterioadenosine 在 氯化亚砜 作用下， 以 六甲基磷酰三胺 为溶剂， 以60%的产率得到5'-chloro-5'-deoxyadenosine-3'-d
  参考文献：
  名称：

  Mechanism of action of S-adenosyl-L-homocysteine hydrolase. Measurement of kinetic isotope effects using adenosine-3'-d and S-adenosyl-L-homocysteine-3'-d as substrates

  摘要：

  DOI：

  10.1021/ja00311a066
• 作为产物：
  描述：

  9-(2,5-di-O-tert-butyldimethylsilyl-β-D-erythro-pentofuran-3-ulosyl)adenosine 在 硼氘化钠 、 四丁基氟化铵 、 水 、 溶剂黄146 、 三氟乙酸 作用下， 反应 2.0h， 生成 3'-deuterioadenosine
  参考文献：
  名称：

  Nucleic acid-related compounds. 58. Periodinane oxidation, selective primary deprotection, and remarkably stereoselective reduction of tert-butyldimethylsilyl-protected ribonucleosides. Synthesis of 9-(.beta.-D-xylofuranosyl)adenine or 3'-deuterioadenosine from adenosine

  摘要：

  DOI：

  10.1021/jo00289a004

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.
• Nucleic Acid-Related Compounds. 88. Efficient Conversions of Ribonucleosides into Their 2',3'-Anhydro, 2'(and 3')-Deoxy, 2',3'-Didehydro-2',3'-dideoxy, and 2',3'-Dideoxynucleoside Analogs
  作者：Morris J. Robins、John S. Wilson、Danuta Madej、Nicholas H. Low、Fritz Hansske、Stanislaw F. Wnuk

  DOI：10.1021/jo00129a034

  日期：1995.12

  Treatment of purine, pyrimidine, and modified purine (antibiotic) ribonucleosides with 2-acetoxy-2-methylpropanoyl (alpha-acetoxyisobutyryl) bromide in acetonitrile gave mixtures of 2',3'-bromohydrin acetates with different O5' substituents. Significant amounts of 5'-unprotected (hydroxyl) bromo acetates were obtained in some cases, and formation of 2',3'-O-isopropylidene derivatives as minor byproducts was detected for the first time. Acid-catalyzed nucleophilic displacement of chloride by bromide occurred with 2-amino-6-chloropurine riboside, but no substitution of fluoride by bromide was detected with 6-amino-2-fluoropurine riboside. Treatment of the trans bromo acetate mixtures obtained from purine-type nucleosides with Dowex 1 x 2 (OH-) in methanol gave the 2',3'-anhydro (ribo epoxide) compounds. Radical-mediated hydrogenolytic debromination and deprotection gave 2'- and 3'-deoxynucleosides. Treatment of the bromo acetate mixtures with zinc-copper couple or acetic acid-activated zinc effected reductive elimination, and deprotection gave 2',3'-didehydro-2',3'-dideoxy compounds which were hydrogenated to give 2',3'-dideoxynucleosides. A number of these analogues have potent inhibitory activity against AIDS and hepatitis B viruses. New C-13 NMR data for several types of unsaturated-sugar nucleosides are tabulated. These procedures are directly applicable for the preparation of L-didehydro-dideoxy and L-dideoxy nucleoside analogues.
• A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2′-ene and 2t',3′-dideoxynucleosides
  作者：Morris J. Robins、Fritz Hansske、Nicholas H. Low、Ja In Park

  DOI：10.1016/s0040-4039(00)99885-x

  日期：1984.1