Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-[1-(dimethylamino-methyleneamino)-6-thioxo-1,6-dihydro-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester | 189155-13-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-[1-(dimethylamino-methyleneamino)-6-thioxo-1,6-dihydro-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
• CAS: 189155-13-3
• 化学式: C₂₀H₂₄N₆O₆S₂
• 分子量: 508.579
• InChiKey: ZRRZNAIAZGIAQV-KLICCBINSA-N

物化性质

• 沸点：
  798.3±70.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-[1-(dimethylamino-methyleneamino)-6-thioxo-1,6-dihydro-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 在 Dowex AG 50W-X₈ NH₄⁺ 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 乙腈 为溶剂， 反应 90.0h， 以67%的产率得到ammonium 1-N-[(dimethylamino)methylene]-6-thioinosine-5'-diphosphate
  参考文献：
  名称：

  The Role of Hydrophobic Versus Hydrophilic Base Character in the Anti-HIV Activity of Purine-Containing Polyribonucleotides

  摘要：

  In contrast to the highly amphiphilic poly(1-methyl-6-thioinosinic acid), a potent anti-HIV agent, poly(1-amino-6-thioinosinic acid) (PATI) lacks the unique melting behavior characteristic of the amphiphilic polymers and is completely devoid of anti-HIV activity. This is consistent with the hypothesis that amphiphilic character and the ability to form an ordered secondary structure in solution are prerequisites for potent anti-HIV activity of single-stranded polynucleotides.

  DOI：

  10.1080/07328319708002531
• 作为产物：
  描述：

  1-amino-6-thioinosine 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-[1-(dimethylamino-methyleneamino)-6-thioxo-1,6-dihydro-purin-9-yl]-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  The Role of Hydrophobic Versus Hydrophilic Base Character in the Anti-HIV Activity of Purine-Containing Polyribonucleotides

  摘要：

  In contrast to the highly amphiphilic poly(1-methyl-6-thioinosinic acid), a potent anti-HIV agent, poly(1-amino-6-thioinosinic acid) (PATI) lacks the unique melting behavior characteristic of the amphiphilic polymers and is completely devoid of anti-HIV activity. This is consistent with the hypothesis that amphiphilic character and the ability to form an ordered secondary structure in solution are prerequisites for potent anti-HIV activity of single-stranded polynucleotides.

  DOI：

  10.1080/07328319708002531