N6-benzoyl-9-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)adenine | 355819-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N6-benzoyl-9-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)adenine
• 英文别名: N⁶-benzoyl-9-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)adenine；2',3'-Di-O-acetyl-9-(α+β)-d-erythro-furanosyl-6-benzamido-purin；2',3'-Di-O-acetyl-9-(α+β)-l-erythro-furanosyl-6-benzamido-purin；O²,O³-diacetyl-1-(6-benzoylamino-purin-9-yl)-β-L-1-deoxy-erythrofuranose
• CAS: 355819-43-1
• 化学式: C₂₀H₁₉N₅O₆
• 分子量: 425.401
• InChiKey: MFCMFQRIWKTIMX-AKCHCHLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  134.53
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N6-benzoyl-9-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)adenine 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 9-β-D-erythrofuranosyladenine
  参考文献：
  名称：

  (13C)-Substituted erythronucleosides: synthesis and conformational analysis by proton and carbon-13 NMR spectroscopy

  摘要：

  The erythronucleosides, 9-beta-D-erythrofuranosyladenine (1b), 1-beta-D-erythrofuranosylcytosine (2b), 9-beta-D-erythrofuranosylguanine (3b), and 1-beta-D-erythrofuranosyluracil (4b), were synthesized with and without C-13-substitution at C1' of the furanose ring. 75-MHz C-13 and 620-MHz H-1 NMR spectra of 1-4b were interpreted, in the latter case with the assistance of spectral simulation, and H-1-H-1, C-13-H-1, and C-13-C-13 spin couplings were used to assess furanose conformation. 3J(HH) data in (H2O)-H-2 were treated by computer to determine the preferred north and south conformers, their puckering amplitudes, and their mole fractions in solution, and J(CH) data were used to complement this analysis. A similar treatment of spin coupling data for the corresponding ribonucleosides 1-4a was also conducted to permit a comparison of furanose conformations in both series of compounds. Results show that the removal of the exocyclic hydroxymethyl group from 1-4a, giving 1-4b, significantly enhances the proportion of south conformers in aqueous ((H2O)-H-2) solution.

  DOI：

  10.1021/jo00032a032
• 作为产物：
  描述：

  2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)- 、 N6-苯甲酰基腺嘌呤 在 N,O-双三甲硅基乙酰胺 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 0.83h， 以80%的产率得到N6-benzoyl-9-(2',3'-di-O-acetyl-β-D-erythrofuranosyl)adenine
  参考文献：
  名称：

  具有包含核碱基的主链的寡核苷酸类似物：第 6 部分，2-脱氧-D-赤藓糖衍生的亚磷酰胺：合成和掺入 14-Mer DNA 链

  摘要：

  Two modified DNA 14-mers have been prepared, containing either a 2-deoxy-D-erythrose-derived adenosine analogue carrying a C(8)-CH2O group (deA*). or a 2-deoxy-D-erpthrose-derived uridine analogue, possessing a C(6)-CH2O group (deU*). These nucleosides are linked via a phosphinato group between O-C(3') (deA* and deU*) and O-C(5') of one neighbouring nucleotide, and between C(8)-CH2O (deA*),or C(6)-CH2O (deU*) and O-C(3') of the second neighbour. N-6-Benzoyl-9-(beta -D-erythrofuranosyl)adeine (3) and 1-(beta -D-erythrofuranosyl)uracil (4) were prepared from D-glucose, deoxygenated at C(2'), and converted into the required phosphoramidites 1 and 2. The modified tetradecamers 31 and 32 were prepared by solid-phase synthesis. Pairing studies show a decrease in the melting temperature of 7 to 8 degrees for the duplexes 31 30 and 32 29, as compared to the unmodified DNA duplex 29 30. A comparison with the pairing properties of tetradecamers similarly incorporating deoxyribose- instead of the deoxyerythrose-derived nucleotides evidences that the CH2OH substituent at C(4') has no significant effect on the pairing.

  DOI：

  10.1002/1522-2675(20010516)84:5<1000::aid-hlca1000>3.0.co;2-s

文献信息

• Base-Pairing Systems Related to TNA:  α-Threofuranosyl Oligonucleotides Containing Phosphoramidate Linkages¹
  作者：Xiaolin Wu、Sreenivasulu Guntha、Mathias Ferencic、Ramanarayanan Krishnamurthy、Albert Eschenmoser

  DOI：10.1021/ol020015x

  日期：2002.4.1

  [GRAPHIC](3'NH)- and (2'NH)-TNA, two isomeric phosphoramidate analogues of TNA (alpha-threofuranosyl-(3'-->2') oligonucleotides), are shown to be efficient Watson-Crick base-pairing systems and to undergo intersystem cross-pairing with TNA, RNA, and DNA.