2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil | 292037-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil
• 英文别名: 2,2'-O-anhydrouridine；O²,2'-anhydro-1-(β-D-arabinofuranosyl)uracil；2,2'-anhydrouridine；O²-2'-Anhydrouridin；2,2'-anhydro-β-D-arabinofuranosyluridine；(2R,4R,5R,6S)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodec-11-en-10-one
• CAS: 292037-79-7
• 化学式: C₉H₁₂N₂O₅
• 分子量: 228.205
• InChiKey: KFYRNEIOTJPFNO-HXQZNRNWSA-N

物化性质

• 沸点：
  613.5±55.0 °C(Predicted)
• 密度：
  1.66±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil 在 Lindlar's catalyst 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 、 氨 、 氢气 、 一氯化碘 、 三乙胺 作用下， 以 喹啉 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 苯 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 13.25h， 生成 1-(beta-D-阿拉伯呋喃糖基)-5-[(E)-2-碘乙烯基]-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  核酸相关化合物。65.由乙烯基硅烷前体合成1-（β-D-阿拉伯呋喃糖基）-5（E）-（2-碘乙烯基）尿嘧啶（IVAraU）。放射性碘的摄取可作为胸苷激酶阳性疱疹病毒感染的标志物。

  摘要：

  将（三甲基甲硅烷基）乙炔与1-（2,3,5-三-O-乙酰基-β-D-阿拉伯呋喃糖基）-5-碘尿嘧啶偶联，得到1-（2,3,5-三-O-乙酰基-β -D-阿拉伯呋喃糖基）-5- [2-（三甲基甲硅烷基）乙氧基]尿嘧啶。4的Lindlar氢化得到1-（2,3,4-三-O-乙酰基-β-D-阿拉伯呋喃糖基）-5（Z）-[2-（三甲基甲硅烷基）乙烯基]尿嘧啶。用苯中的一氯化碘（或碘化钠/二氯化苯基碘（III））处理5，得到1-（2,3,5-三-O-乙酰基-β-D-阿拉伯呋喃糖基）-5（E）-（2-碘乙烯基）尿嘧啶（7），而极性溶剂偏爱（Z）-碘乙烯基异构体8 。用Na * I进行的微型原位合成得到[* I] IVAraU。用[125I] IVAraU处理被HSV感染的细胞会导致病毒依赖性摄取，与野生型或抗阿昔洛韦的DNA聚合酶突变体（但不包括TK-HSV-1突变体）的核苷磷酸化有关。摄取是病毒-菌落

  DOI：

  10.1021/jm00111a050
• 作为产物：
  描述：

  尿嘧啶核苷 在 碳酸二苯酯 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以90%的产率得到2,2'-anhydro-1-(β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  2'-O-烷基嘧啶核糖核苷的高效大规模合成

  摘要：

  已经描述了一种以高产率合成 2'-O-烷基嘧啶核糖核苷的有效方法。廉价的方法用于多公斤级合成和优化反应...

  DOI：

  10.1021/op990100t

文献信息

• A new protecting group ‘3′,5′-O-sulfinyl’ for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine
  作者：Ken-ichi Takatsuki、Makoto Yamamoto、Sumito Ohgushi、Shigeo Kohmoto、Keiki Kishikawa、Haruhiro Yamashita

  DOI：10.1016/j.tetlet.2003.10.092

  日期：2004.1

  We developed a new protecting group, the cyclic sulfite for the protection of the 3′,5′-dihydroxy group of nucleosides. Seven cyclic sulfites, 4a–c, 5a–b, and 6a–b were prepared in high yields from the corresponding xylo-uridines 1 and 2, and xylo-adenosines 3 with thionyl chloride, respectively. Synthesis of the puromycin intermediate 8 was carried out by deprotection of the sulfite moiety through

  我们开发了一种新的保护基团，为保护3的循环亚'，5 '核苷的二羟基组。分别由相应的木尿苷1和2以及木苷腺苷3和亚硫酰氯分别高产率地制备了七个环状亚硫酸盐4a – c，5a – b和6a – b。嘌呤霉素中间体的合成8是由亚硫酸盐部分的脱保护通过2的分子内环化进行' -α -氨基甲酸酯7。
• Novel Dideoxynucleoside Derivatives
  申请人：Kitade Yukio

  公开号：US20080064868A1

  公开（公告）日：2008-03-13

  The present invention discloses a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside derivative represented by the following formula [1]: (wherein R 1 represents a nucleic acid base which may have a protecting group; R 2 represents a hydrogen atom or a protecting group of an amino group; R 3 represents a hydrogen atom or a protecting group of a hydroxyl group); a dideoxynucleoside-insoluble carrier bound substance prepared by binding said dideoxynucleoside derivative to an insoluble carrier, and an oligonucleotide analogue into which said dideoxynucleoside derivative is introduced. The oligonucleotide analogue being introduced with a dideoxynucleoside derivative of the present invention has excellent thermal stability and also high binding affinity when duplex is formed. Also, it is anticipated that it has high resistance to nucleases. Further, the dideoxynucleoside derivative of the present invention can be used as an amidite reagent to be used for nucleic acid synthesis, and also as a starting material for solid phase synthesis of nucleic acid by binding the amidite reagent to a solid phase.

  本发明公开了由下式[1]所表示的5'-氨基-2'-氟-2',5'-二脱氧核苷衍生物（其中R1表示可能具有保护基团的核酸碱基；R2表示氢原子或氨基的保护基团；R3表示氢原子或羟基的保护基团）；通过将该二脱氧核苷衍生物与不溶性载体结合而制备的二脱氧核苷载体结合物质；以及引入了该二脱氧核苷衍生物的寡核苷酸类似物。本发明引入了含有该二脱氧核苷衍生物的寡核苷酸类似物具有优异的热稳定性，当形成双链时也具有高结合亲和力。此外，预计它具有高核酸酶抵抗力。此外，本发明的二脱氧核苷衍生物可用作用于核酸合成的酰胺酯试剂，也可作为将酰胺酯试剂结合到固相上进行核酸固相合成的起始物料。
• Comparative investigations on thermostable pyrimidine nucleoside phosphorylases from Geobacillus thermoglucosidasius and Thermus thermophilus
  作者：Kathleen Szeker、Xinrui Zhou、Thomas Schwab、Ana Casanueva、Don Cowan、Igor A. Mikhailopulo、Peter Neubauer

  DOI：10.1016/j.molcatb.2012.02.006

  日期：2012.12

  The recombinant expression and biocatalytic characterization of two thermostable pyrimidine nucleoside phosphorylases (PyNP), isolated from Geobacillus thermoglucosidasius (Gt) and Thermus thermophilus (Tt) is described. Both enzymes are highly thermostable (half life of GtPyNP is 1.6 h at 70 °C, half life of TtPyNP is >24 h at 80 °C). Kinetic parameters for the phosphorolysis of natural substrates

  描述了从热葡萄糖芽孢杆菌（Gt）和嗜热栖热菌（Tt）分离的两种热稳定嘧啶核苷磷酸化酶（PyNP）的重组表达和生物催化特性。两种酶都具有很高的热稳定性（在70°C下，GtPyNP的半衰期为1.6小时，在80°C下，TtPyNP的半衰期为> 24 h）。确定为天然底物的磷酸解的动力学参数为GtPyNP在60°C（ķ米尿苷2.3毫米，ķ米胸苷1.3毫摩尔）和TtPyNP在80°C（ķ米尿苷0.15毫米，ķ米胸苷0.43毫米）。该ķ猫两种酶的尿苷值几乎相同（约277 s -1），而TtPyNP的胸苷的k cat值是GtPyNP的k cat值的约8倍（679 s -1对83 s -1）。
• Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists
  作者：Hyojin Ko、Rhonda L. Carter、Liesbet Cosyn、Riccardo Petrelli、Sonia de Castro、Pedro Besada、Yixing Zhou、Loredana Cappellacci、Palmarisa Franchetti、Mario Grifantini、Serge Van Calenbergh、T. Kendall Harden、Kenneth A. Jacobson

  DOI：10.1016/j.bmc.2008.05.013

  日期：2008.6

  The phosphate, uracil, and ribose moieties of uracil nucleotides were varied structurally for evaluation of agonist activity at the human P2Y(2), P2Y(4), and P2Y(6) receptors. The 2-thio modi. cation, found previously to enhance P2Y2 receptor potency, could be combined with other favorable modi. cations to produce novel molecules that exhibit high potencies and receptor selectivities. Phosphonomethylene bridges introduced for stability in analogues of UDP, UTP, and uracil dinucleotides markedly reduced potency. Truncation of dinucleotide agonists of the P2Y(2) receptor, in the form of Up(4)-sugars, indicated that a terminal uracil ring is not essential for moderate potency at this receptor and that specific SAR patterns are observed at this distal end of the molecule. Key compounds reported in this study include 9, alpha, beta-methylene-UDP, a P2Y(6) receptor agonist; 30, Up(4)-phenyl ester and 34, Up(4)-[1] glucose, selective P2Y(2) receptor agonists; dihalomethylene phosphonate analogues 16 and 41, selective P2Y(2) receptor agonists; 43, the 2-thio analogue of INS37217 (P-1-(uridine-5')-P-4-(2'-deoxycytidine-5') tetraphosphate), a potent and selective P2Y(2) receptor agonist. Published by Elsevier Ltd.