2-(N,N-diphenylcarbamoyl)oxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine | 180477-13-8

• 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: 2-(N,N-diphenylcarbamoyl)oxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine
• 英文别名: [9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl] N,N-diphenylcarbamate
• CAS: 180477-13-8
• 化学式: C₂₃H₂₁N₅O₅
• 分子量: 447.45
• InChiKey: HTJWXSJKCRPQTA-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  122.83
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-(N,N-diphenylcarbamoyl)oxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 0.5h， 生成 2-(N,N-diphenylcarbamoyl)oxy-9-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-9H-purine 3'-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine

  摘要：

  The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.

  DOI：

  10.1080/15257770008045448
• 作为产物：
  描述：

  Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(2-hydroxy-purin-9-yl)-tetrahydro-furan-3-yl ester 在 ammonium hydroxide 、 sodium hydroxide 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 1.5h， 生成 2-(N,N-diphenylcarbamoyl)oxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purine
  参考文献：
  名称：

  Thermal stability studies of the non canonical base pair between 5-methyl-isocytosine and isohypoxanthine

  摘要：

  The hybridization properties of 5-methyl-isocytosine ((5Me)isoC) and isohypoxanthine (isoI) have been investigated by using ultraviolet melting techniques. These two bases were incorporated into heptadecanucleotides using the phosphoramidite chemistry. The base pair (5Me)isoC/isoI was found to be isoenergetic with the A/T base pair. A small destabilization was observed when isoI was located opposite T or G and can be interpreted by a pairing mode between these bases and isoI in its lactam form. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00820-5