N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine | 61289-19-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine
• 英文别名: 1-methyl-5-(tri-O-acetyl-β-D-ribofuranosyl)-1H-pyrimidine-2,4-dione；O^2'_,O3'_,O5'-triacetyl-1-methyl-pseudouridine；1-Methylpseudouridintriacetat；[(2R,3R,4S,5S)-3,4-diacetyloxy-5-(1-methyl-2,4-dioxopyrimidin-5-yl)oxolan-2-yl]methyl acetate
• CAS: 61289-19-8
• 化学式: C₁₆H₂₀N₂O₉
• 分子量: 384.343
• InChiKey: RJIVBOSDMQEYOV-RQJABVFESA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine 在 偶氮二异丁腈 、 四丁基氟化铵 、 氨 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 35.5h， 生成 5-(2-脱氧-BETA-D-赤式-呋喃戊糖基)-1-甲基-2,4(1H,3H)-嘧啶二酮
  参考文献：
  名称：

  A Practical Synthesis ofN1-Methyl-2′-deoxy-ψ-uridine (ψ-Thymidine) and Its Incorporation into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of N1-methyl-2'-deoxy-psi-uridine (psi-thymidine, psi T, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of the modified TFOs (S4, S5 and S6) containing psi T has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(CTGAGACCGGGAAGGAGGAAGGGCCAGTGAC)3'-5d(GACTCTGGCCCTTCCTCCTTCCCGGTCACTG)3' (D1) at pH 7.6. The tripler formation of modified homopyrimidine-oligomers (S1, S2 and S3) has also been studied in parallel motif with a duplex-10 (A(10):T-10) at pH 7.0.

  DOI：

  10.1080/15257779508010690
• 作为产物：
  描述：

  假尿苷 在 苯磺酰胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N1-methyl-2',3',5'-tri-O-acetyl-ψ-uridine
  参考文献：
  名称：

  A Practical Synthesis ofN1-Methyl-2′-deoxy-ψ-uridine (ψ-Thymidine) and Its Incorporation into G-Rich Triple Helix Forming Oligonucleotides

  摘要：

  A convenient synthesis of N1-methyl-2'-deoxy-psi-uridine (psi-thymidine, psi T, 7a) has been accomplished in good yield. The structural conformation of 7a was derived by 2D NMR and 1D NOE experiments. The nucleoside 7a has been incorporated into G-rich tripler forming oligonucleotides (TFOs) by solid-support, phosphoramidite method. The tripler forming capabilities of the modified TFOs (S4, S5 and S6) containing psi T has been evaluated in antiparallel motif with a target duplex (duplex-31) 5'd(CTGAGACCGGGAAGGAGGAAGGGCCAGTGAC)3'-5d(GACTCTGGCCCTTCCTCCTTCCCGGTCACTG)3' (D1) at pH 7.6. The tripler formation of modified homopyrimidine-oligomers (S1, S2 and S3) has also been studied in parallel motif with a duplex-10 (A(10):T-10) at pH 7.0.

  DOI：

  10.1080/15257779508010690

文献信息

• 1-Methylpseudouridine, a metabolite of Streptomyces platensis.
  作者：A. D. ARGOUDELIS、S. A. MIZSAK

  DOI：10.7164/antibiotics.29.818

  日期：——

  1-Methylpseudouridine is a new metabolite isolated from culture filtrates of Streptomyces platensis. The structure of this compound was determined from its physical and spectral properties.

  1-甲基嘌呤核苷酸是从链霉菌（Streptomyces platensis）培养液滤液中分离出来的新代谢产物。通过物理和光谱特性确定了这种化合物的结构。