(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol | 35638-82-5

• 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: (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol
• 英文别名: 2'-O-benzyladenosine；O^2'-benzyl-adenosine；9-(2-O-Benzyl-β-D-ribofuranosyl)adenin；2'-O-Benzyl-adenosin；2'-O-Benzyladenosin；Adenosine, 2'-O-(phenylmethyl)-；(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-phenylmethoxyoxolan-3-ol
• CAS: 35638-82-5
• 化学式: C₁₇H₁₉N₅O₄
• 分子量: 357.369
• InChiKey: GUCMSLDJFPHTIR-LSCFUAHRSA-N

物化性质

• 熔点：
  150-151.5 °C
• 沸点：
  678.5±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以100%的产率得到腺苷
  参考文献：
  名称：

  A New Method for the Synthesis of 2′-O-Benzyladenosine Using Mitsunobu Reaction

  摘要：

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.

  DOI：

  10.1081/ncn-120019506
• 作为产物：
  描述：

  9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine 在 氨 作用下， 以 甲醇 为溶剂， 生成 (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-(benzyloxy)-5-(hydroxymethyl) tetrahydrofuran-3-ol
  参考文献：
  名称：

  Introduction of a Benzyl Group onto the 2′-OH of 6-Chloropurine 3′-O-Benzoylriboside

  摘要：

  A new method to introduce a benzyl group onto the 2'-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3'-O-benzoylriboside and its 5'-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2'-O-benzyl derivative. The yields were varied from 4.6 to 62.9%, depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2' is retained.

  DOI：

  10.1081/ncn-120022633

文献信息

• Compositions and methods for detecting and modulating rna activity and gene expression
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP1418179A2

  公开（公告）日：2004-05-12

  Compositions and methods for modulating the activity of RNA and DNA are disclosed. In accordance with preferred embodiments, antisense compositions are prepared comprising targeting and reactive portions. Reactive portions which act, alternatively, through phosphorodiester bond cleavage, through backbone sugar bond cleavage or through base modification are preferably employed. Groups which improve the pharmacodynamic and pharmacokinetic properties of the oligonucleotides are also useful in accordance with certain embodiments of this invention. Delivery of the reactive or non-reactive functionalities into the minor groove formed by the hybridization of the composition with the target RNA is also preferably accomplished. Therapeutics, diagnostics and research methods are also disclosed. Synthetic nucleosides and nucleoside fragments are also provided useful for elaboration of oligonucleotides and oligonucleotide analogs for such purposes.

  本文公开了调节 RNA 和 DNA 活性的组合物和方法。根据优选的实施方案，反义组合物由靶向部分和反应部分组成。反应部分最好通过磷酸二酯键裂解、骨架糖键裂解或碱基修饰起作用。根据本发明的某些实施方案，改善寡核苷酸药效学和药代动力学特性的基团也是有用的。最好还能将反应性或非反应性官能团输送到组合物与目标 RNA 杂交形成的次凹槽中。本发明还公开了治疗、诊断和研究方法。本发明还提供了合成核苷和核苷片段，可用于制备用于上述目的的寡核苷酸和寡核苷酸类似物。
• Structure-Guided Design of a Methyl Donor Cofactor That Controls a Viral Histone H3 Lysine 27 Methyltransferase Activity
  作者：Jiaojie Li、Hua Wei、Ming-Ming Zhou

  DOI：10.1021/jm201000j

  日期：2011.11.10

  vSET (a viral SET domain protein) is an attractive polycomb repressive complex 2 (PRC2) surrogate to study the effect of histone H3 lysine 27 (H3K27) methylation on gene transcription, as both catalyze histone H3K27 trimethylation. To control the enzymatic activity of vSET in vivo with an engineered S-adenosyl-L-methionine (SAM) analogue as methyl donor cofactor, we have carried out structure-guided design, synthesis, and characterization of orthogonal vSET methyltransferase mutant/ SAM analogue pairs using a "bump-and-hole" strategy.
• Mizuno, Yoshihisa; Endo, Takeshi; Takahashi, Akira, Chemical and pharmaceutical bulletin, 1980, vol. 28, # 10, p. 3041 - 3048
  作者：Mizuno, Yoshihisa、Endo, Takeshi、Takahashi, Akira、Inaki, Atsuko

  DOI：——

  日期：——
• OLIGONUCLEOTIDE ANALOGS FOR DETECTING AND MODULATING RNA ACTIVITY AND GENE EXPRESSION
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：EP0604409B1

  公开（公告）日：2004-07-14
• Development of a chemical scaffold for inhibiting nonribosomal peptide synthetases in live bacterial cells
  作者：Fumihiro Ishikawa、Sho Konno、Hideaki Kakeya、Genzoh Tanabe

  DOI：10.3762/bjoc.20.39

  日期：——

  The adenylation (A) domain is essential for non-ribosomal peptide synthetases (NRPSs), which synthesize various peptide-based natural products, including virulence factors, such as siderophores and genotoxins. Hence, the inhibition of A-domains could attenuate the virulence of pathogens. 5’-O-N-(Aminoacyl or arylacyl)sulfamoyladenosine (AA-AMS) is a bisubstrate small-molecule inhibitor of the A-domains of NRPSs. However, the bacterial cell permeability of AA-AMS is typically a problem owing to its high hydrophilicity. In this study, we investigated the influence of a modification of 2′-OH in the AMS scaffold with different functional groups on binding to target enzymes and bacterial cell penetration. The inhibitor 7 with a cyanomethyl group at 2′-OH showed desirable inhibitory activity against both recombinant and intracellular gramicidin S synthetase A (GrsA) in the gramicidin S-producer Aneurinibacillus migulanus ATCC 9999, providing an alternative scaffold to develop novel A-domain inhibitors.