5'-Deoxy-5'-methylsulphonyladenosine | 5143-04-4

• 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'-Deoxy-5'-methylsulphonyladenosine
• 英文别名: Methyl--sulfon；5'-methanesulfonyl-5'-deoxy-adenosine；S-methyl-5'-thio-adenosine S,S-dioxide；(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfonylmethyl)oxolane-3,4-diol
• CAS: 5143-04-4
• 化学式: C₁₁H₁₅N₅O₅S
• 分子量: 329.337
• InChiKey: KSVWCZPIQZUJSJ-IOSLPCCCSA-N

物化性质

• 熔点：
  205-207 °C(Solv: water (7732-18-5))
• 沸点：
  775.0±70.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-Deoxy-5'-methylsulphonyladenosine 在 phosphate buffer pH 6.8 、 乙硫醇 作用下， 以 水 为溶剂， 以76%的产率得到5'-deoxy-5'-(methylsulfonyl)inosine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 82. Conversions of Adenosine to Inosine 5′-Thioether Derivatives withAspergillus oryzaeAdenosine Deaminase or Alkyl Nitrites. Substrate and Inhibitory Activities of Inosine 5′-Thioether Derivatives with Purine Nucleoside Phosphorylase

  摘要：

  Adenosine derivatives lacking a 5'-hydroxyl group seldom act as alternative substrates of adenosine deaminases from calf intestine and other mammalian sources. A deaminase from Aspergillus oryzae deaminated adenosine 5'-thioether derivatives cleanly and more efficiently than alkyl nitrites. The inosine derivatives were very poor alternative substrates and weak inhibitors of purine nucleoside phosphorylase.

  DOI：

  10.1080/15257779408013249
• 作为产物：
  描述：

  甲硫腺苷 在 双氧水 、 溶剂黄146 作用下， 生成 (2R,3R,4S,5S)-2-(6-氨基嘌呤-9-基)-5-(甲基亚磺酰甲基)四氢呋喃-3,4-二醇 、 5'-Deoxy-5'-methylsulphonyladenosine
  参考文献：
  名称：

  S-腺苷-L-蛋氨酸类似物的合成和评估，作为大肠杆菌环丙烷脂肪酸合酶的抑制剂。

  摘要：

  合成了S-腺苷-L-蛋氨酸类似物，并作为纯化的大肠杆菌环丙烷脂肪酸合酶的抑制剂进行了评估，该酶是结核分枝杆菌环丙烷合酶的模型，是抗结核药物的潜在靶标。我们的结果表明，抑制剂中必须存在腺苷部分才能牢固结合，但是sulf电荷的重要性不高。发现的最佳抑制剂是S-腺苷-1-高半胱氨酸及其亚砜。

  DOI：

  10.1016/j.bmcl.2004.01.051

文献信息

• Synthesis and evaluation of analogues of S-adenosyl-l-methionine, as inhibitors of the E. coli cyclopropane fatty acid synthase
  作者：Christine Guérard、Maud Bréard、Fabienne Courtois、Thierry Drujon、Olivier Ploux

  DOI：10.1016/j.bmcl.2004.01.051

  日期：2004.4

  synthesized and evaluated as inhibitors of the purified E. coli cyclopropane fatty acid synthase, a model for M. tuberculosis cyclopropane synthases that are potential targets for antituberculous drugs. Our results show that the presence of the adenosine moiety, in the inhibitor, is required for strong binding, but that the sulfonium charge is less important. The best inhibitors found were S-adenosyl-l-homocysteine

  合成了S-腺苷-L-蛋氨酸类似物，并作为纯化的大肠杆菌环丙烷脂肪酸合酶的抑制剂进行了评估，该酶是结核分枝杆菌环丙烷合酶的模型，是抗结核药物的潜在靶标。我们的结果表明，抑制剂中必须存在腺苷部分才能牢固结合，但是sulf电荷的重要性不高。发现的最佳抑制剂是S-腺苷-1-高半胱氨酸及其亚砜。
• Nucleic Acid Related Compounds. 82. Conversions of Adenosine to Inosine 5′-Thioether Derivatives with<i>Aspergillus oryzae</i>Adenosine Deaminase or Alkyl Nitrites. Substrate and Inhibitory Activities of Inosine 5′-Thioether Derivatives with Purine Nucleoside Phosphorylase
  作者：Stanislaw F. Wnuk、Johanna D. Stoeckler、Morris J. Robins

  DOI：10.1080/15257779408013249

  日期：1994.3

  Adenosine derivatives lacking a 5'-hydroxyl group seldom act as alternative substrates of adenosine deaminases from calf intestine and other mammalian sources. A deaminase from Aspergillus oryzae deaminated adenosine 5'-thioether derivatives cleanly and more efficiently than alkyl nitrites. The inosine derivatives were very poor alternative substrates and weak inhibitors of purine nucleoside phosphorylase.