N⁷-(2'-deoxy-β-D-erythro-pentofuranosyl)guanine | 159791-63-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: N⁷-(2'-deoxy-β-D-erythro-pentofuranosyl)guanine
• 英文别名: 7-(2-deoxy-β-D-erythro-pentofuranosyl)-1,7-dihydro-6H-purin-6-one；2-amino-7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 159791-63-6
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: JXQMTPJDEKCVMN-KVQBGUIXSA-N

物化性质

• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 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：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁷-(2'-deoxy-β-D-erythro-pentofuranosyl)guanine 在 三(4-硝基苯基)磷酸酯 作用下， 以73%的产率得到Phosphoric acid mono-[(2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-7-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl] ester
  参考文献：
  名称：

  Enzymatic 5′-monophosphorylation of modified nucleosides

  摘要：

  DOI：

  10.1007/bf00598099
• 作为产物：
  描述：

  2-脱氧-1-乙酸-3,5-二苯甲酸-D-赤式-五呋喃糖 在 二苯并-18-冠醚-6 、 氨 、 potassium iodide 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 N⁷-(2'-deoxy-β-D-erythro-pentofuranosyl)guanine
  参考文献：
  名称：

  2'-脱氧核糖核苷的区域特异性合成的改进程序

  摘要：

  通过用KI-二苯并-18-冠-6 PTC催化未保护的甲硅烷基化的嘌呤和嘧啶与适当的易得的2-脱氧核糖呋喃糖基或吡喃糖基糖衍生物之间的缩合，可以高特异性合成2'-脱氧核糖核苷。

  DOI：

  10.1016/s0040-4039(00)97641-x

文献信息

• Studies on the Base-Pairing Properties ofN7-(2-Deoxy-?-D-erythro-pentofuranosyl)guanine (N7Gd)
  作者：Frank Seela、Peter Leonard

  DOI：10.1002/hlca.19970800424

  日期：1997.6.30

  amine (3d) was used, whereas 6-(2-methoxyethoxy)purin-2-arnine (3i) gave mainly the N9-nucleoside (2:1). Oligonucleotides containing compound 1 were prepared by solid-phase synthesis and hybridized with complementary strands having the four conventional nucleosides located opposite to N7Gd. According to Tm values and enthalpy data of duplex formation, a base pair between N7Gd and dG is suggested. From

  研究了N 7-（2-脱氧-β-D-赤型戊呋喃糖基）鸟嘌呤（N 7 G d；1）的碱基配对性质。通过核苷碱基阴离子糖基化获得核苷1。研究了各种6-烷氧基嘌呤-2-胺3a - i与2-脱氧-3,5-二-O-（4-甲苯甲酰基）-α-D-赤型-戊呋喃糖酰氯的糖基化反应（8）。所述Ñ 9 / Ñ 7 -glycosylation比率被发现是1：1时6- isopropoxypurin -2-胺（3D），而6-（2-甲氧基乙氧基）嘌呤-2-亚胺（3i）主要产生N 9-核苷（2：1）。通过固相合成制备含有化合物1的寡核苷酸，并将其与具有四个与N 7 G d相对的常规核苷的互补链杂交。根据双链形成的T m值和焓数据，提出了N 7 G d和dG之间的碱基对。从可能的N 7 G d dG碱基对动机出发，Hoogsteen配对可以被排除，因为7-脱氮基2'-脱氧鸟苷与N 7 G d形成与dG相同的稳定碱基对。
• N7-DNA: Synthesis and Base Pairing of Oligonucleotides ContainingN7-(2-Deoxy-?-D-erythro-pentofuranosyl)guanine (N7Gd)
  作者：Frank Seela、Peter Leonard

  DOI：10.1002/hlca.19960790215

  日期：1996.3.20

  The synthesis of oligonucleotides containing N7-(2-deoxy-β-D-erythro-pentofuranosyl)guanine (N7Gd; 1) is described. Compound 1 was prepared by nucleobase-anion glycosylation of 2-amino-6-methoxypurine (5) with 2-deoxy-3,5-di-O-(4-toluoyl)-α-D-erythro-pentofuranosyl chloride (6) followed by detoluoylation and displacement of the MeO group (8101). Upon base protection with the (dimethylamino)methylidene

  描述了含有N 7-（2-脱氧-β-D-赤型-呋喃呋喃糖基）鸟嘌呤（N 7 G d；1）的寡核苷酸的合成。化合物1的制备是通过将2-氨基-6-甲氧基嘌呤（核碱基阴离子糖基化5与2-脱氧-3,5-二- ）Ö - （4-甲苯酰基）-α-D-赤式-pentofuranosyl酰氯（6）接着是去甲苯甲酸酯化和MeO基团的置换（8101）。用（二甲基氨基）亚甲基残基（11）进行碱保护后，将4,4-二甲氧基三苯甲基引入OHC（5'）（12）。制备膦酸酯3和亚磷酰胺4，并将其用于固相寡核苷酸合成中。自互补十二聚体d（N 7 GC）6显示出S型熔化。双工的T m为40°。这表明通过嘌呤的N（7）与磷酸二酯主链连接的鸟嘌呤残基能够与胞嘧啶进行碱基配对。
• The ThermalN9/N7 Isomerization ofN2-Acylated 2′-Deoxyguanosine Derivatives in the Melt and in Solution
  作者：Bozenna Golankiewicz、Tomasz Ostrowski、Peter Leonard、Frank Seela

  DOI：10.1002/1522-2675(200201)85:1<388::aid-hlca388>3.0.co;2-e

  日期：2002.1

  The protected 2'-deoxyguanosine derivatives 5a - c undergo N-9 --> N-7 isomerization in the melt and in solution, The rate of isomerization is much faster than in the case of the corresponding, ribonucleosides and occurs even in the absence of a catalyst. In the melt (195. 2 min), the N-2.3'-O.5'-O-tris(4-toluoyl) derivative -% and the N-2-acetyl-3',5'-bis-O-[(tert-butyl)dimethylsilyl] derivative 5c gave anomeric mixtures of the,V-isomers 9b/10b) (43%) and 9c/10c (55%). respectively, In addition, the N-9-alpha-D-anomers 8b and 8c are obtained. Different from 5b, the isomerization of peracetylated 5a resulted in low yields. Compound 5b was also prone tu isomerization performed in solution (toluene. 100, 5 min: chlorobenzene, 120. 5 min). furnishing the N-7-regioisomers in 24-53% yield. The highest yield of the N-9 --> N-7 isomerization occurred in the presence of 2-deoxy-3,5-di-O-(4-toluoyl)-alpha-D-erythro-pentofuranosyl chloride.
• Heikkilä; Stridh; Oberg, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1985, vol. 39, # 8, p. 657 - 669
  作者：Heikkilä、Stridh、Oberg、Chattopadhyaya

  DOI：——

  日期：——
• N7-DNA: Base-Pairing Properties ofN7-(2′-Deoxy-β-D-erythro-pentofuranosyl)-Substituted Adenine, Hypoxanthine, and Guanine in Duplexes with Parallel Chain Orientation
  作者：Frank Seela、Peter Leonard

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2244::aid-hlca2244>3.0.co;2-i

  日期：1998.12.16