5'-对甲苯磺酰基-2'-脱氧胞苷 | 27999-55-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: 5'-对甲苯磺酰基-2'-脱氧胞苷
• 英文名称: 2'-Deoxy-5'-O-tosylcytidin
• 英文别名: O^5'-(toluene-4-sulfonyl)-2'-deoxy-cytidine；O^5'-(Toluol-4-sulfonyl)-2'-desoxy-cytidin；5'-Tosyl-2'-deoxy Cytidine；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 27999-55-9
• 化学式: C₁₆H₁₉N₃O₆S
• 分子量: 381.409
• InChiKey: IENUZDCEUIARIF-GZBFAFLISA-N

物化性质

• 熔点：
  >135°C (dec.)
• 沸点：
  631.5±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Bu4N)3 OMDP 、 5'-对甲苯磺酰基-2'-脱氧胞苷 在 DOWEX AG-50W column (NH₄⁺) form 作用下， 以 乙腈 、 水 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT

  摘要：

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.

  DOI：

  10.1021/jm800692a
• 作为产物：
  描述：

  对甲苯磺酰氯 、 2'-脱氧胞嘧啶核苷 在 吡啶 作用下， 反应 16.0h， 生成 5'-对甲苯磺酰基-2'-脱氧胞苷
  参考文献：
  名称：

  α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT

  摘要：

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.

  DOI：

  10.1021/jm800692a

文献信息

• Andersen et al., Journal of the Chemical Society, 1954, p. 1882,1884
  作者：Andersen et al.

  DOI：——

  日期：——
• METHOD OF OBTAINING OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES, AN ANTI-AGING COMPOSITION AND USE OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES IN THE MANUFACTURE OF ANTI-AGING COMPOSITION
  申请人：Instytut Chemii Bioorganicznej PAN

  公开号：EP2225228A2

  公开（公告）日：2010-09-08
• [EN] METHOD OF OBTAINING OF 4-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES, AN ANTI-AGING COMPOSITION AND USE OF 4-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES IN THE MANUFACTURE OF ANTI-AGING COMPOSITION<br/>[FR] PROCÉDÉ D'OBTENTION DE 4-FURFURYLCYTOSINE ET/OU DE SES DÉRIVÉS, COMPOSITION ANTIVIEILLISSEMENT ET UTILISATION DE LA 4-FURFURYLCYTOSINE ET/OU DE SES DÉRIVÉS DANS LA FABRICATION D'UNE COMPOSITION ANTIVIEILLISSEMENT
  申请人：INST CHEMII BIOORG PAN

  公开号：WO2009067035A2

  公开（公告）日：2009-05-28

  The subjects of the present invention are the method of preparation of 4-furfurylcytosine and/or its derivatives, its use in the manufacture of anti-aging compositions and an anti- aging composition. As 4-furfurylcytosine and/or its derivatives possesses a series of biological properties it might be use as a composition having excellent anti-aging effect to prevent the sagging of skin and loss of luster and to improve sufficiently its aesthetic appearance without significantly change the growth rate and the total growth ability of the skin. Optimal methods of manufacturing this compound, while at the same time obtaining the highest possible process efficiency, with particular emphasis on its utility in the pharmaceutical and cosmetic industries are presented.
• α,β-Methylene-2′-deoxynucleoside 5′-Triphosphates as Noncleavable Substrates for DNA Polymerases: Isolation, Characterization, and Stability Studies of Novel 2′-Deoxycyclonucleosides, 3,5′-Cyclo-dG, and 2,5′-Cyclo-dT
  作者：Fengting Liang、Nidhi Jain、Troy Hutchens、David D. Shock、William A. Beard、Samuel H. Wilson、M. Paul Chiarelli、Bongsup P. Cho

  DOI：10.1021/jm800692a

  日期：2008.10.23

  We report synthesis and characterization of a complete set of alpha,beta-methylene-2'-dNTPs (alpha,beta-m-dNTP; N = A, C, T, G, 12-15) in which the alpha,beta-oxygen linkage of natural dNTP was replaced by a methylene group. These nucleotides were designed to be noncleavable substrates for DNA polymerases. Synthesis entails preparation of 2'-deoxynucleoside 5'-diphosphate precursors, followed by an enzymatic gamma-phosphorylation. All four synthesized alpha,beta-m-dNTPs were found to be potent inhibitors of polymerase beta, with K-i values ranging 1-5 mu M. During preparation of the dG and dT derivatives of alpha,beta-methylene diphosphate, we also isolated significant amounts of 3,5'-cyclo-dG (16) and 2,5'-cyclo-dT (17), respectively. These novel 2'-deoxycyclonucleosides were formed via a base-catalyzed intramolecular cyclization (N3 -> C5' and O2 -> C5' respectively). In acidic solution, both 16 and 17 underwent glycolysis, followed by complete depurination. When exposed to alkaline conditions, 16 underwent an oxidative deamination to produce 3,5'-cyc1o-2'-deoxyxanthosine (19), whereas 17 was hydrolyzed exclusively to dT.