9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ol

• 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: 9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ol
• 英文别名: 2'-Deoxyisoinosine；9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-2-one
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: YOLSYNLZAPCTKP-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ol 在 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 2-(N,N-diphenylcarbamoyl)oxy-9-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-9H-purine
  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：

  2-amino-9-(2-deoxy-β-D-ribofuranosyl)purine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以83%的产率得到9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-ol
  参考文献：
  名称：

  2'-脱氧异肌苷及相关2'-脱氧核糖核苷的合成

  摘要：

  制备了在C（2）具有甲硫基（13a），氯（13b），甲氧基（9b）和氧代（2、3）取代基的各种2-取代的嘌呤和吡咯并[2,3 - d ]嘧啶2'-脱氧核糖核苷。它们可以通过立体选择性核碱基阴离子糖基化或碱基转化获得。描述了由2'-脱氧鸟苷（15）三步合成未知的2'-脱氧异肌氨酸（2）。化合物2及其7-脱氮嘌呤衍生物3显示强荧光。

  DOI：

  10.1002/hlca.19940770122

文献信息

• Thermal stability studies of the non canonical base pair between 5-methyl-isocytosine and isohypoxanthine
  作者：Jean-Jacques Beaussire、Sylvie Pochet

  DOI：10.1016/s0040-4020(98)00820-5

  日期：1998.10

  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.
• 2'-Deoxyisoinosine: Synthesis of a Highly Fluorescent Nucleoside and Its Incorporation into Oligonucleotides
  作者：Frank Seela、Yaoming Chen

  DOI：10.1080/15257779508012490

  日期：1995.5.1

  The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'-dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.
• Chemical and Enzymatic Synthesis of 2'-Deoxy-iso-inosine and Its Incorporation into DNA
  作者：Jean-Jacques Beaussire、Sylvie Pochet

  DOI：10.1080/15257779508012476

  日期：1995.5.1

  Two procedures for the preparation of 2'-deoxy-iso-inosine (1) are presented. Synthesis of 3'-phosphoramidite (7) and 3'-phosphonate (8) derivatives are described, as well as an oligodeoxynucleotide containing iso-I.
• Seela, Frank; Chen, Yaoming; Sauer, Markus, Nucleosides and Nucleotides, 1998, vol. 17, # 1-3, p. 39 - 52
  作者：Seela, Frank、Chen, Yaoming、Sauer, Markus

  DOI：——

  日期：——
• Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine
  作者：Frank Seela、Georg Becher、Yaoming Chen

  DOI：10.1080/15257770008045448

  日期：2000.10

  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.