7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purin-6-one | 29868-32-4

• 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: 7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purin-6-one
• 英文别名: N⁷-(2'-deoxy-β-D-erythro-pentofuranosyl)adenine；2'-deoxy-N⁷-inosine；7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 29868-32-4
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: KLKIRPUROSYHAE-RRKCRQDMSA-N

物化性质

• 熔点：
  208-209 °C(Solv: water (7732-18-5))
• 沸点：
  744.7±60.0 °C(Predicted)
• 密度：
  1.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 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：
  6

反应信息

• 作为反应物：
  描述：

  7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purin-6-one 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 7-<5-O--2-deoxy-β-D-erythro-pentofuranosyl>-1,7-dihydro-6H-purin-6-one-3'-<(2-cyanoethyl)diisopropylphosphoramidite>
  参考文献：
  名称：

  N7-DNA: Base-Pairing Properties ofN7-(2′-Deoxy-β-D-erythro-pentofuranosyl)-Substituted Adenine, Hypoxanthine, and Guanine in Duplexes with Parallel Chain Orientation

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19981216)81:12<2244::aid-hlca2244>3.0.co;2-i
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 氢氧化钾 、 sodium hydroxide 、 三(3,6-二氧杂庚基)胺 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 7.33h， 生成 7-<2-deoxy-β-D-erythro-pentofuranosyl>-7H-purin-6-one
  参考文献：
  名称：

  Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer

  摘要：

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.

  DOI：

  10.1080/15257779508014658

文献信息

• Enzymatic synthesis of ribo- and 2′-deoxyribonucleosides from glycofuranosyl phosphates: An approach to facilitate isotopic labeling
  作者：Wenhui Zhang、Toby Turney、Ivana Surjancev、Anthony S. Serianni

  DOI：10.1016/j.carres.2017.07.006

  日期：2017.9

  Milligram quantities of α-D-ribofuranosyl 1-phosphate (sodium salt) (αR1P) were prepared by the phosphorolysis of inosine, catalyzed by purine nucleoside phosphorylase (PNPase). The αR1P was isolated by chromatography in >95% purity and characterized by 1H and 13C NMR spectroscopy. Aqueous solutions of αR1P were stable at pH 6.4 and 4 °C for several months. The isolated αR1P was N-glycosylated with

  通过嘌呤核苷磷酸化酶（PNPase）催化的肌苷磷酸分解，制备了毫克量的α-D-呋喃呋喃糖基1-磷酸钠盐（αR1P）。通过色谱法以> 95％的纯度分离出αR1P，并通过1H和13C NMR光谱进行了表征。αR1P​​水溶液在pH 6.4和4°C下稳定了几个月。使用PNPase或尿苷磷酸化酶（UPase），将分离的αR1P用不同的氮碱基（腺嘌呤，鸟嘌呤和尿嘧啶）进行N-糖基化，从而基于糖基磷酸酯以高收率得到相应的核糖核苷。该方法对于稳定同位素标记的核糖核糖核苷和2'-脱氧核糖核苷的制备具有吸引力，因为其产品纯化简便，氮碱的使用和回收方便。该方法消除了制备单独的呋喃糖标记的核糖核苷的单独反应的需要，因为如果需要，在呋喃糖环中仅需要标记一个核糖核苷（肌苷），后者可以通过高产率的化学N-糖基化来实现。使用相同的方法，由2'-脱氧肌苷制备2'-脱氧核糖核苷，并稍作改动。
• 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
• Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer
  作者：Frank Seela、Holger Winter

  DOI：10.1080/15257779508014658

  日期：1995.2

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.