5'-S-phenyl-5'-thioadenosine | 5135-37-5

• 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'-S-phenyl-5'-thioadenosine
• 英文别名: S-phenyl-5'-thio-adenosine；Phenyl--sulfid；5'-Phenylthio-5'-deoxyadenosin；(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(phenylsulfanylmethyl)oxolane-3,4-diol
• CAS: 5135-37-5
• 化学式: C₁₆H₁₇N₅O₃S
• 分子量: 359.409
• InChiKey: QVFVRQNGWNWFTF-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-S-phenyl-5'-thioadenosine 在 phosphate buffer pH 6.8 、 乙硫醇 作用下， 以 水 为溶剂， 以78%的产率得到5'-S-phenyl-5'-thioinosine
  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：

  5'-chloro-5'-deoxy-2',3'-O-sulphinyladenosine hydrochloride 在 ammonium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5'-S-phenyl-5'-thioadenosine
  参考文献：
  名称：

  Nucleic acid related compounds. 66. Improved syntheses of 5′-chloro-5′-deoxy- and 5′-S-aryl(or alkyl)-5′-thionucleosides

  摘要：

  使用硫酰氯/吡啶/乙腈（0°C至室温）处理核糖核苷可基本定量形成5'-氯-5'-脱氧-2'，3'-O-亚磺酰核苷衍生物。这些对映异构的亚硫酸酯酯可以轻松地通过甲醇氨水溶液去保护基。这样就可以不使用疑似致癌物六甲基磷酰胺（HMPA）制备5'-氯-5'-脱氧核苷。在二甲基甲酰胺中，通过钠硫醇的亲核置换反应（-30°C至室温），可以高产得到5'-S-芳基（或烷基）-5'-硫代核苷。使用硫酰氯/乙腈而不是吡啶处理核糖核苷，然后进行水处理，可以得到未修饰的5'-羟基核苷的对映异构的2'，3'-O-亚磺酰核苷。文中还提到了环状亚硫酸酯立体化学的诊断NMR位移。关键词：腺苷，5'-S-芳基（或烷基）-5'-硫代核苷，5'-氯-5'-脱氧核苷，尿苷，核苷。

  DOI：

  10.1139/v91-217

文献信息

• Design, synthesis, and biological evaluation of novel human 5′-deoxy-5′-methylthioadenosine phosphorylase (MTAP) substrates
  作者：Pei-Pei Kung、Luke R. Zehnder、Jerry J. Meng、Stanley W. Kupchinsky、Donald J. Skalitzky、M. Catherine Johnson、Karen A. Maegley、Anne Ekker、Leslie A. Kuhn、Peter W. Rose、Laura A. Bloom

  DOI：10.1016/j.bmcl.2005.03.107

  日期：2005.6

  The structure-based design, chemical synthesis, and biological evaluation of novel MTAP substrates are described. These compounds incorporate various C5'-moieties and are shown to have different k(cat)/K values compared with the natural MTAP substrate (MTA). (c) 2005 Elsevier Ltd. All rights reserved.
• Fluorination at C5′ of nucleosides. Synthesis of the new class of 5′-fluoro-5′-S-aryl (alkyl) thionucleosides from adenosine.
  作者：Morris J. Robins、Wnuk F. Stanislaw

  DOI：10.1016/s0040-4039(00)82174-7

  日期：1988.1
• Nucleic Acid Related Compounds. 80. Synthesis of 5'-S-(Alkyl and aryl)-5'-fluoro-5'-thioadenosines with Xenon Difluoride or (Diethylamido)sulfur Trifluoride, Hydrolysis in Aqueous Buffer, and Inhibition of S-Adenosyl-L-homocysteine hydrolase by derived "Adenosine 5'-Aldehyde" Species
  作者：Morris J. Robins、Stanislaw F. Wnuk、Khairuzzaman B. Mullah、N. Kent Dalley、Chong-Sheng Yuan、Younha Lee、Ronald T. Borchardt

  DOI：10.1021/jo00082a010

  日期：1994.2

  Treatment of 5/-S-(alkyl and aryl)-5'-thioadenosine derivatives 2 with XeF2, or the corresponding sulfoxides 3 with DAST/SbCl3, gave diastereomeric 5'-fluoro compounds which were deprotected to give the 5'-S-(alkyl and aryl)-5'-fluoro-5'-thioadenosine analogues 5. Stereochemistry was established by X-ray crystallography, and F-19 NMR chemical shifts were definitive for configurationally-related 5'-fluoro diastereomers. Sulfoxidation and thermolysis afforded the fluoromethylene analogues with retained relative configuration. The nucleoside 5'-alpha-fluoro thioethers 5 underwent spontaneous hydrolysis in aqueous buffer to give derived ''adenosine 5'-aldehyde'' species which caused potent time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase.
• ROBINS, MORRIS J.;WNUK, STANISLAW F., TETRAHEDRON LETT., 29,(1988) N 45, C. 5729-5732
  作者：ROBINS, MORRIS J.、WNUK, STANISLAW F.

  DOI：——

  日期：——
• Nucleic acid related compounds. 66. Improved syntheses of 5′-chloro-5′-deoxy- and 5′-<i>S</i>-aryl(or alkyl)-5′-thionucleosides
  作者：Morris J. Robins、Fritz Hansske、Stanislaw F. Wnuk、Tadashi Kanai

  DOI：10.1139/v91-217

  日期：1991.9.1

  Treatment of ribonucleosides with thionyl chloride/pyridine/acetonitrile (0 °C to ambient temperature) resulted in essentially quantitative formation of 5′-chloro-5′-deoxy-2′,3′-O-sulfinylnucleoside derivatives. These diastereomeric sulfite esters underwent deprotection readily with aqueous methanolic ammonia. This gave 5′-chloro-5′-deoxynucleosides without use of the suspected carcinogen, hexamethylphosphoramide (HMPA). Nucleophilic displacement with sodium thiolates in dimethylformamide (−30 °C to ambient temperature) gave 5′-S-aryl(or alkyl)-5′-thionucleosides in high yields. Treatment of ribonucleosides with thionyl chloride/acetonitrile without pyridine followed by aqueous work-up gave diastereomeric 2′,3′-O-sulfinylnucleosides with an unmodified 5′-hydroxyl group. Diagnostic NMR shifts for cyclic sulfite ester stereochemistry are noted. Key words: adenosine, 5′-S-aryl(or alkyl)-5′-thionucleosides, 5′-chloro-5′-deoxynucleosides, uridine, nucleosides.

  使用硫酰氯/吡啶/乙腈（0°C至室温）处理核糖核苷可基本定量形成5'-氯-5'-脱氧-2'，3'-O-亚磺酰核苷衍生物。这些对映异构的亚硫酸酯酯可以轻松地通过甲醇氨水溶液去保护基。这样就可以不使用疑似致癌物六甲基磷酰胺（HMPA）制备5'-氯-5'-脱氧核苷。在二甲基甲酰胺中，通过钠硫醇的亲核置换反应（-30°C至室温），可以高产得到5'-S-芳基（或烷基）-5'-硫代核苷。使用硫酰氯/乙腈而不是吡啶处理核糖核苷，然后进行水处理，可以得到未修饰的5'-羟基核苷的对映异构的2'，3'-O-亚磺酰核苷。文中还提到了环状亚硫酸酯立体化学的诊断NMR位移。关键词：腺苷，5'-S-芳基（或烷基）-5'-硫代核苷，5'-氯-5'-脱氧核苷，尿苷，核苷。