1-(3-C-methyl-β-D-ribofuranosyl)uracil 5'-triphosphate | 87215-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-C-methyl-β-D-ribofuranosyl)uracil 5'-triphosphate
• 英文别名: 3'-c-Methyluridine 5'-triphosphate；[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-3-methyloxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 87215-07-4
• 化学式: C₁₀H₁₇N₂O₁₅P₃
• 分子量: 498.171
• InChiKey: IWXMULPYZRPAJC-AMCGLFBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  259
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 三甲基氯硅烷 、 2,4,6-三异丙基苯磺酰氯 、 三正丁胺 、 2-cyanoethyl pyridinium phosphate 、 硫酸 、 四氯化锡 、 三丁基焦磷酸铵 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 六甲基二硅氮烷 、 N,N'-羰基二咪唑 、 zinc(II) chloride 作用下， 以 吡啶 、 甲醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 288.33h， 生成 1-(3-C-methyl-β-D-ribofuranosyl)uracil 5'-triphosphate
  参考文献：
  名称：

  3'-C-甲基核苷及其磷酸酯的合成及性质

  摘要：

  摘要从d-葡萄糖开始，经11个步骤合成了3'-C-甲基尿苷和3'-C-甲基胞苷。使用cd，1 Hn.mr光谱和X射线衍射分析技术研究了溶液和晶体中3'-C-甲基核苷的构象。制备了3'-C-甲基尿苷2'，3'-环磷酸酯，并对其进行了核酸酶水解研究。还合成了3'-C-甲基尿苷5'-单磷酸酯和5'-三磷酸酯。

  DOI：

  10.1016/0008-6215(83)88357-8

文献信息

• 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.
• Synthesis and properties of 3′-C-methylnucleosides and their phosphoric esters
  作者：Sergey N. Mikhailov、Leon N. Beigelman、Galyna V. Gurskaya、Nelly Sh. Padyukova、Gennady I. Yakovlev、Marat Ya. Karpeisky

  DOI：10.1016/0008-6215(83)88357-8

  日期：1983.12

  Abstract 3′- C -Methyluridine and 3′- C -methylcytidine were synthesized in 11 steps starting from d -glucose. The conformation of 3′- C -methylnucleosides was studied in solution and in the crystal by using the techniques of c.d., 1 H-n.m.r. spectroscopy, and X-ray diffraction analysis. 3′- C -Methyluridine 2′,3′-cyclophosphate was prepared, and its hydrolysis with nucleases was studied. 3′- C -Methyluridine

  摘要从d-葡萄糖开始，经11个步骤合成了3'-C-甲基尿苷和3'-C-甲基胞苷。使用cd，1 Hn.mr光谱和X射线衍射分析技术研究了溶液和晶体中3'-C-甲基核苷的构象。制备了3'-C-甲基尿苷2'，3'-环磷酸酯，并对其进行了核酸酶水解研究。还合成了3'-C-甲基尿苷5'-单磷酸酯和5'-三磷酸酯。