1-(2-deoxy-2-fluoro-β-D-xylofuranosyl)thymine | 601512-79-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2-deoxy-2-fluoro-β-D-xylofuranosyl)thymine
• 英文别名: 1-[(2R,3R,4S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2R,3R,4S,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 601512-79-2
• 化学式: C₁₀H₁₃FN₂O₅
• 分子量: 260.222
• InChiKey: GBBJCSTXCAQSSJ-JAGXHNFQSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-2-fluoro-β-D-xylofuranosyl)thymine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 1-(3-O-((2-cyanoethoxy)(N,N-diisopropylamino)phosphino)-2-deoxy-5-O-(4,4'-dimethoxytrityl)-2-fluoro-β-D-xylofuranosyl)thymine
  参考文献：
  名称：

  xylo-configured寡核苷酸（XNA，xylo核酸）：合成和杂交研究。

  摘要：

  我们报告的合成和完全修饰的家庭胸腺嘧啶2'-脱氧和2'-脱氧-2'-氟木糖核酸的高亲和力杂交。

  DOI：

  10.1081/ncn-120022822
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 23.0h， 生成 1-(2-deoxy-2-fluoro-β-D-xylofuranosyl)thymine
  参考文献：
  名称：

  Xylo-Configured oligonucleotides (XNA, xylo nucleic acid): synthesis of conformationally restricted derivatives and hybridization towards DNA and RNA complements

  摘要：

  Xylo-Configured oligonucleotides (XNA) containing a novel conformationally restricted 2'-deoxy-2'-fluoro-beta-D-xylofuranosyl nucleotide monomer, a novel conformationally locked 2'-amino-2'-deoxy-2'-N,4'-C-methylene-beta-D-xylofuranosyl nucleotide monomer. and a known 2'-deoxy-beta-D-xylofuranosyl nucleotide monomer (XNA monomers) have been synthesized and their hybridization towards DNA and RNA complements studied. Thermal denaturation studies of nine-mer mixed-base sequences composed of a mixture of XNA monomers and DNA monomers revealed preferential hybridization towards RNA complements relative to DNA complements. For 14-mer homo-thymine XNAs containing thirteen XNA monomers, stable complexes towards single-stranded DNA and RNA were formed at pH 7. Gel-shift experiments revealed these complexes to involve at least two XNA strands per DNA or RNA target strand. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00441-4

文献信息

• Antiviral Activity of Various 1-(2′-Deoxy-β-<scp>d</scp>-lyxofuranosyl), 1-(2′-Fluoro-β-<scp>d</scp>-xylofuranosyl), 1-(3′-Fluoro-β-<scp>d</scp>-arabinofuranosyl), and 2′-Fluoro-2′,3′-didehydro-2′,3′-dideoxyribose Pyrimidine Nucleoside Analogues against Duck Hepatitis B Virus (DHBV) and Human Hepatitis B Virus (HBV) Replication
  作者：Naveen C. Srivastav、Neeraj Shakya、Michelle Mak、Babita Agrawal、D. Lorne Tyrrell、Rakesh Kumar

  DOI：10.1021/jm100803c

  日期：2010.10.14

  3′-fluoroarabinofuranosyl, and 2′-fluoro-2′,3′-didehydro-2′,3′-dideoxyribose pyrimidine nucleoside analogues for antiviral activities against hepatitis B virus. Among the compounds examined, 1-(2-deoxy-β-d-lyxofuranosyl)thymine (23), 1-(2-deoxy-β-d-lyxofuranosyl)-5-trifluoromethyluracil (25), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)uracil (38), 1-(2-deoxy-2-fluoro-β-d-xylofuranosyl)thymine (39), 2′,3′-dideoxy-2′,3′-d

  尽管存在成功的疫苗和抗病毒疗法，但乙型肝炎病毒（HBV）的感染仍然是急性和慢性肝病以及高死亡率的全球主要原因。我们合成并评估了几种lyxofuranosyl，2'-fluorooxylofuranosyl，3'-fluoroarabinofuranosyl和2'-fluoro-2'，3'-didehydro-2'，3'-dideoxyribose嘧啶核苷类似物对乙型肝炎病毒的抗病毒活性。在所检查的化合物中，1-（2-脱氧-β - d-呋喃呋喃糖基）胸腺嘧啶（23），1-（2-脱氧-β - d-呋喃呋喃糖基）-5-三氟甲基尿嘧啶（25），1-（2-脱氧-2-氟-β - d-木呋喃糖基）尿嘧啶（38），1-（2-脱氧-2-氟-β- d-二呋喃呋喃糖基）胸腺嘧啶（39），2'，3'-二脱氧-2'，3'-二脱氢-2'-氟胸苷（48）和2'，3'-二脱氧-2'，3'-二脱氢-2在原代鸭肝细胞中发现'
• [EN] MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS OLIGOMÈRES MODIFIÉS ET LEURS UTILISATIONS
  申请人：IONIS PHARMACEUTICALS INC

  公开号：WO2021030763A1

  公开（公告）日：2021-02-18

  The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

  本公开提供了包含至少一种立体非标准核苷酸的修饰寡核苷酸的寡聚化合物。包括由12-30个连接的核苷酸组成的修饰寡核苷酸的寡聚化合物，其中修饰寡核苷酸的至少一个核苷酸是立体非标准核苷酸；且所述寡聚化合物选自RNAi化合物、修饰CRISPR化合物和人工mRNA化合物。
• XNA (xylo Nucleic Acid): A Summary and New Derivatives
  作者：B. Ravindra Babu、Raunak、Nicolai E. Poopeiko、Martin Juhl、Andrew D. Bond、Virinder S. Parmar、Jesper Wengel

  DOI：10.1002/ejoc.200500023

  日期：2005.6

  furanose conformation. Besides, an efficient synthesis of known xylo-LNA phosphoramidite 19, required for the incorporation of 1-(2'-O,4'-C-methylene-β-D-xylofuranosyl)thymine (monomer L) is described. For comparison, hydridization data of various XNAs reported in the literature are included in the discussion section. The thermal denaturation studies show that XNAs containing conformationally locked

  完全修饰的同型嘧啶 2'-脱氧-木核酸 (dXNA) 与互补的 DNA/RNA 形成三螺旋，其热稳定性与相应的 DNA:DNA 和 DNA:RNA 双链体的热稳定性相当。然而，在 DNA 链中插入单个或几个 dXNA 单体会显着降低双链体的稳定性。已知 dXNA 单体在溶液中主要采用 N 型呋喃糖构象。为了提高结合亲和力，已经合成了七种糖修饰的 XNA 单体（H、F、N、M、K、P 和 Q），并研究了它们对 DNA 和 RNA 互补物杂交的影响。预计引入 2'-氟和 2'-羟基取代基会导致对衍生自 1-(2'-deoxy-2' 的单体 F 的 C3'-内型呋喃糖构象的构象限制 -氟-β-D-呋喃木糖基）胸腺嘧啶和衍生自 1-（β-D-呋喃木糖基）胸腺嘧啶的单体 H。存在面向小沟的官能团，如 1-(2'-amino-2'-deoxy-2'-N,4'-C-methylene-β-D-xylofuranosyl)thymine